1-(5-chloro-2,4-dihydroxyphenyl)-2-(2-methoxyphenyl)ethanone | 1226799-00-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(5-chloro-2,4-dihydroxyphenyl)-2-(2-methoxyphenyl)ethanone
• 英文别名: 1-(5-chloro-2,4-dihydroxy-phenyl)-2-(2-methoxy-phenyl)-ethanone
• CAS: 1226799-00-3
• 化学式: C₁₅H₁₃ClO₄
• 分子量: 292.719
• InChiKey: YAAHFGHVSYTNQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-chloro-2,4-dihydroxyphenyl)-2-(2-methoxyphenyl)ethanone 在 aluminum (III) chloride 、 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 6-chloro-7-hydroxy-3-(2-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  顺式-罗汉果的 合成，光学拆分，绝对构型和成骨活性†

  摘要：

  通过三个步骤即可轻松合成天然和合成的罗汉松。通过在手性固定相上进行分析和半制备性HPLC来完成各个对映异构体的旋光拆分。对于麦地卡宾及其合成衍生物9-去甲氧基medicarpin，绝对构型已通过实验性LC-ECD耦合和量子化学ECD计算的结合得到证实。（-）-Medicarpin和（-）-9-demethoxymedicarpin都是6a R，11a R-构型，因此相应的对映异构体（+）-medicarpin和（+）-9-demethoxymedicarpin具有6a S，11a S -配置。麦地卡因的骨形成（骨形成）活性的比较机制研究（外消旋与对映体纯净的材料）显示（+）-（6a S，11a S）-medicarpin（6a）显着增加了骨形态发生蛋白2（BMP2）的表达和骨特异性转录因子Runx-2 mRNA的水平，而对于其他对映异构体（-）-（6a R，11a R）-medicarpi

  DOI：

  10.1039/c2ob25722j
• 作为产物：
  描述：

  4-氯间苯二酚 、 2-甲氧基苯乙酸 在 三氟化硼乙醚 作用下， 反应 2.0h， 以60%的产率得到1-(5-chloro-2,4-dihydroxyphenyl)-2-(2-methoxyphenyl)ethanone
  参考文献：
  名称：

  顺式-罗汉果的 合成，光学拆分，绝对构型和成骨活性†

  摘要：

  通过三个步骤即可轻松合成天然和合成的罗汉松。通过在手性固定相上进行分析和半制备性HPLC来完成各个对映异构体的旋光拆分。对于麦地卡宾及其合成衍生物9-去甲氧基medicarpin，绝对构型已通过实验性LC-ECD耦合和量子化学ECD计算的结合得到证实。（-）-Medicarpin和（-）-9-demethoxymedicarpin都是6a R，11a R-构型，因此相应的对映异构体（+）-medicarpin和（+）-9-demethoxymedicarpin具有6a S，11a S -配置。麦地卡因的骨形成（骨形成）活性的比较机制研究（外消旋与对映体纯净的材料）显示（+）-（6a S，11a S）-medicarpin（6a）显着增加了骨形态发生蛋白2（BMP2）的表达和骨特异性转录因子Runx-2 mRNA的水平，而对于其他对映异构体（-）-（6a R，11a R）-medicarpi

  DOI：

  10.1039/c2ob25722j

文献信息

• [EN] SUBSTITUTED BENZFUROCHROMENES AND RELATED COMPOUNDS FOR THE PREVENTION AND TREATMENT OF BONE RELATED DISORDERS<br/>[FR] BENZOFUROCHROMÈNES SUBSTITUÉS ET COMPOSÉS APPARENTÉS POUR LA PRÉVENTION ET LE TRAITEMENT DE TROUBLES LIÉS AUX OS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010052734A1

  公开（公告）日：2010-05-14

  The present invention relates to novel substituted benzfurochromenes and related compounds having the general formula (I), salts and chiral, achiral derivatives thereof; wherein R1, R2, R3, R4, R5, R6, R7, R8 are independently selected from the groups consisting of hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkylthio, optionally substituted amino, optionally substituted acylamino, optionally substituted arylamino, optionally substituted acylthio, optionally substituted acyl, optionally substituted aroyl, optionally substituted acyloxy, optionally substituted thioamido, halogens, nitriles, esters, hydroxy, mercapto, carbontrifluoride, nitro but not limited to this; wherein R1R2 or R2R3 or R6R7 may be connected and form either a five membered ring or a six membered ring such as optionally substituted furan, optionally substituted dihydrofuran, optionally substituted pyran; or may be connected through a methylenedeoxy moiety; wherein X is selected from the units consisting of optionally a ketone group, optionally a methylene group, optionally substituted methylene group, optionally substituted alkene; wherein Y and Z is selected from the units consisting of CH, C-OH, C-Me, C-OMe with the proviso that bond between Y and Z is a single bond; Wherein Y and Z may be a carbon atom with the proviso that bond between Y and Z is a double bond;. The compounds of the general formula is useful for the prevention and treatment of bone related disorders.

  本发明涉及新型取代苯并呋色烯和相关化合物，其具有一般式(I)，其盐和手性、无手性衍生物；其中R1、R2、R3、R4、R5、R6、R7、R8分别独立地选自氢、可选择取代的烷基、可选择取代的烯基、可选择取代的烷氧基、可选择取代的芳基、可选择取代的杂芳基、可选择取代的硫代烷基、可选择取代的氨基、可选择取代的酰胺基、可选择取代的芳基胺基、可选择取代的酰硫代基、可选择取代的酰基、可选择取代的芳酰基、可选择取代的酰氧基、可选择取代的硫酰胺基、卤素、腈、酯、羟基、巯基、三氟甲基、硝基等；其中R1R2或R2R3或R6R7可能连接并形成五元环或六元环，例如可选择取代的呋喃、可选择取代的二氢呋喃、可选择取代的吡喃；或可通过亚甲基脱氧基团连接；其中X选自可选择酮基、可选择亚甲基、可选择取代的亚甲基、可选择取代的烯烃基；其中Y和Z选自CH、C-OH、C-Me、C-OMe单位，但Y和Z之间的键为单键；其中Y和Z可以是碳原子，但Y和Z之间的键为双键。一般式化合物对预防和治疗与骨相关的疾病有用。
• SUBSTITUTED BENZFUROCHROMENES AND RELATED COMPOUNDS FOR THE PREVENTION AND TREATMENT OF BONE RELATED DISORDERS
  申请人：Goel Atul

  公开号：US20120003273A1

  公开（公告）日：2012-01-05

  The present invention relates to novel substituted benzfurochromenes and related compounds having the general formula (I), salts and chiral, achiral derivatives thereof; wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are independently selected from the groups consisting of hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkylthio, optionally substituted amino, optionally substituted acylamino, optionally substituted arylamino, optionally substituted acylthio, optionally substituted acyl, optionally substituted aroyl, optionally substituted acyloxy, optionally substituted thioamido, halogens, nitriles, esters, hydroxy, mercapto, carbontrifluoride, nitro but not limited to this; wherein R 1 R 2 or R 2 R 3 or R 6 R 7 may be connected and form either a five membered ring or a six membered ring such as optionally substituted furan, optionally substituted dihydrofuran, optionally substituted pyran; or may be connected through a methylenedeoxy moiety; wherein X is selected from the units consisting of optionally a ketone group, optionally a methylene group, optionally substituted methylene group, optionally substituted alkene; wherein Y and Z is selected from the units consisting of CH, C—OH, C-Me, C—OMe with the proviso that bond between Y and Z is a single bond; Wherein Y and Z may be a carbon atom with the proviso that bond between Y and Z is a double bond. The compounds of the general formula is useful for the prevention and treatment of bone related disorders.

  本发明涉及新的取代苯并呋喃色素和相关化合物，其具有通式（I），其盐和手性、非手性衍生物；其中R1、R2、R3、R4、R5、R6、R7、R8独立地选自由氢、可选取代烷基、可选取代烯基、可选取代烷氧基、可选取代芳基、可选取代杂环芳基、可选取代烷硫基、可选取代氨基、可选取代酰胺基、可选取代芳基氨基、可选取代酰硫基、可选取代酰基、可选取代芳酰基、可选取代酰氧基、可选取代硫代酰胺基、卤素、腈、酯、羟基、巯基、三氟甲基、硝基等，但不限于此；其中R1R2或R2R3或R6R7可以连接并形成五元环或六元环，例如可选取代呋喃、可选取代二氢呋喃、可选取代吡喃；或可以通过甲基氧基连接；其中X选自可选酮基、可选甲基基、可选取代甲基基、可选取代烯基单元；其中Y和Z选自CH、C—OH、C-Me、C—OMe，但在Y和Z之间的键是单键；其中Y和Z可以是碳原子，但在Y和Z之间的键是双键。通式化合物对于预防和治疗与骨相关的疾病有用。
• Substituted benzfurochromenes and related compounds for the prevention and treatment of bone related disorders
  申请人：Goel Atul

  公开号：US08686028B2

  公开（公告）日：2014-04-01

  The present invention relates to novel substituted benzfurochromenes and related compounds having the general formula (I), salts and chiral, achiral derivatives thereof; wherein R1, R2, R3, R4, R5, R6, R7, R8 are independently selected from the groups consisting of hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkylthio, optionally substituted amino, optionally substituted acylamino, optionally substituted arylamino, optionally substituted acylthio, optionally substituted acyl, optionally substituted aroyl, optionally substituted acyloxy, optionally substituted thioamido, halogens, nitriles, esters, hydroxy, mercapto, carbontrifluoride, nitro but not limited to this; wherein R1R2 or R2R3 or R6R7 may be connected and form either a five membered ring or a six membered ring such as optionally substituted furan, optionally substituted dihydrofuran, optionally substituted pyran; or may be connected through a methylenedeoxy moiety; wherein X is selected from the units consisting of optionally a ketone group, optionally a methylene group, optionally substituted methylene group, optionally substituted alkene; wherein Y and Z is selected from the units consisting of CH, C—OH, C-Me, C—OMe with the proviso that bond between Y and Z is a single bond; Wherein Y and Z may be a carbon atom with the proviso that bond between Y and Z is a double bond. The compounds of the general formula is useful for the prevention and treatment of bone related disorders.

  本发明涉及一种新型取代苯并呋喃色酮和相关化合物，其具有通式（I），其盐和手性，非手性衍生物；其中R1，R2，R3，R4，R5，R6，R7，R8独立地选自氢，可选取代烷基，可选取代烯基，可选取代烷氧基，可选取代芳基，可选取代杂环芳基，可选取代烷硫基，可选取代氨基，可选取代酰胺基，可选取代芳基胺基，可选取代酰硫基，可选取代酰基，可选取代芳酰基，可选取代酰氧基，可选取代硫代酰胺，卤素，腈，酯，羟基，巯基，三氟甲基，硝基等，但不仅限于此；其中R1R2或R2R3或R6R7可以连接并形成五元环或六元环，例如可选取代呋喃，可选取代二氢呋喃，可选取代吡喃；或可以通过亚甲基脱氧基团连接；其中X选自可选的酮基团，可选的亚甲基基团，可选取代亚甲基基团，可选取代烯丙基；其中Y和Z选自CH，C-OH，C-Me，C-OMe单元，但应注意Y和Z之间的键为单键；其中Y和Z可以是碳原子，但应注意Y和Z之间的键为双键。通式化合物对于预防和治疗与骨相关的疾病有用。
• SUBSTITUTED BENZFUROCHROMENES FOR THE PREVENTION AND TREATMENT OF BONE RELATED DISORDERS
  申请人：Council Of Scientific & Industrial Research

  公开号：EP2346844B1

  公开（公告）日：2017-09-20
• Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans
  作者：Atul Goel、Amit Kumar、Yasmin Hemberger、Ashutosh Raghuvanshi、Ram Jeet、Govind Tiwari、Michael Knauer、Jyoti Kureel、Anuj K. Singh、Abnish Gautam、Ritu Trivedi、Divya Singh、Gerhard Bringmann

  DOI：10.1039/c2ob25722j

  日期：——

  convenient synthesis of natural and synthetic pterocarpans was achieved in three steps. Optical resolution of the respective enantiomers was accomplished by analytical and semi-preparative HPLC on a chiral stationary phase. For medicarpin and its synthetic derivative 9-demethoxymedicarpin, the absolute configuration was confirmed by a combination of experimental LC-ECD coupling and quantum-chemical ECD

  通过三个步骤即可轻松合成天然和合成的罗汉松。通过在手性固定相上进行分析和半制备性HPLC来完成各个对映异构体的旋光拆分。对于麦地卡宾及其合成衍生物9-去甲氧基medicarpin，绝对构型已通过实验性LC-ECD耦合和量子化学ECD计算的结合得到证实。（-）-Medicarpin和（-）-9-demethoxymedicarpin都是6a R，11a R-构型，因此相应的对映异构体（+）-medicarpin和（+）-9-demethoxymedicarpin具有6a S，11a S -配置。麦地卡因的骨形成（骨形成）活性的比较机制研究（外消旋与对映体纯净的材料）显示（+）-（6a S，11a S）-medicarpin（6a）显着增加了骨形态发生蛋白2（BMP2）的表达和骨特异性转录因子Runx-2 mRNA的水平，而对于其他对映异构体（-）-（6a R，11a R）-medicarpi