3-(3,4-二乙酰氧基苯基)丙酰氯 | 69914-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 3-(3,4-二乙酰氧基苯基)丙酰氯
• 英文名称: 3-(3,4-diacetoxyphenyl)propionyl chloride
• 英文别名: [2-Acetyloxy-4-(3-chloro-3-oxopropyl)phenyl] acetate
• CAS: 69914-81-4
• 化学式: C₁₃H₁₃ClO₅
• 分子量: 284.696
• InChiKey: RPPALXNEJKVQDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4-二乙酰氧基苯基)丙酰氯 在 吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 1,8-dihydroxy-10-[3-(3,4-dihydroxyphenyl)-1-oxopropyl]-9(10H)-anthracenone
  参考文献：
  名称：

  10-Hydrocinnamoyl- and 10-cinnamoyl-1,8-dihydroxy-9(10H)-anthracenones as inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth

  摘要：

  A series of 10-hydrocinnamoyl and 10-cinnamoyl-1,8-dihydroxy-9(10H)-anthracenones has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. In the hydrocinnamoyl series, compounds with phenolic hydroxyl groups were less potent inhibitors of LTB4 biosynthesis than their non-phenolic analogs, suggesting that a nonspecific redox interaction between the compounds and the active site Fe3+ of 5-lipoxygenase or chelation of Fe3+ is not responsible for the observed activity. Compounds bearing a 10-cinnamoyl group were somewhat less active than their less rigid dihydrocinnamoyl congeners. Many compounds were also potent inhibitors of the growth of HaCaT cells with IC50 values in the submicromolar range. Their activity in this assay was equivalent to that observed with the antipsoriatic anthralin, whereas unspecific cytotoxicity was largely reduced as documented by the activity of lactate dehydrogenase released from cytoplasm of keratinocytes. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80021-x

文献信息

• Efficient synthesis of bicyclo[5.3.0]decatrienones and of 2-tetralones via rhodium(<scp>II</scp>) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acids
  作者：M. Anthony McKervey、Sarbajna M. Tuladhar、M. Fiona Twohig

  DOI：10.1039/c39840000129

  日期：——

  Rhodium (II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acid produces bicyclo[5.3.0]decatrienones or 2-tetralones depending on the substitution pattern of the aryl ring: the former products are transformed into the latter by catalytic amount of trifluoroacetic acid.

  乙酸铑（II）催化的3-芳基丙酸衍生的α-二氮酮的环化反应会生成双环[5.3.0]癸二酮或2-四氢萘酮，具体取决于芳基环的取代方式：前者通过催化转化为后者适量的三氟乙酸。
• The intramolecular Buchner reaction of aryl diazoketones. Substituent effects and scope in synthesis
  作者：Michael Kennedy、M. Anthony McKervey、Anita R. Maguire、Sarbajna M. Tuladhar、M. Fiona Twohig

  DOI：10.1039/p19900001047

  日期：——

  cyclisation occurring in all cases. When the precursor contains a meta-methoxy substituent, 2-tetralones are obtained directly. The efficient conversion of 3-phenylpropionic acid into trans-1-methylbicyclo[5.3.0]decan-2-one is also described, partial asymmetric synthesis having been realised through the use of rhodium (S)-mandelate as the cyclisation catalyst. Cyclisations of diazoketones derived from

  根据前驱体中芳基环的取代方式，由铑（II）乙酸催化的3-芳基丙酸衍生的α-二氮酮的环化反应会生成双环[5.3.0]癸二酮或2-四氢萘酮。前者的产物用三氟乙酸催化转化为后者。已经检测了具有甲基，甲氧基和乙酰氧基取代基的前体，在所有情况下均发生有效的环化。当前体含有间-甲氧基取代基时，直接获得2-四氢萘酮。还描述了将3-苯基丙酸有效转化为反-1-甲基双环[5.3.0]癸烷-2-酮，已通过使用铑实现了部分不对称合成（S-扁桃酸酯作为环化催化剂。还研究了由4-苯基丁酸和5-苯基戊酸衍生的重氮酮的环化。前者为双环[5.4.0]十一烷体系提供了新的入口，而后者通过CH的插入产生了2,3-二取代的环戊酮。讨论了稠环系统中环庚三烯-降二十碳烯平衡的各个方面。
• Phenol derivatives for promoting human nerve growth factor
  申请人：Sankyo Company Limited

  公开号：EP0399814A2

  公开（公告）日：1990-11-28

  Phenol derivatives of use in promoting formation of nerve growth factor are of the general formula (Ia) or (Ib) wherein, each R¹ is hydrogen or a hydroxy-protecting group; either R² is alkyl, cycloalkyl, cycloalkyl condensed with aryl, aryl, aralkyl or heterocyclic; and R³ is hydrogen or a group R²; or R² and R³, with the nitrogen atom to which they are attached, represent a cyclic amino group; m is 1 to 6; n is 1 to 3, provided that when n is 2 or 3 then two adjacent groups R¹ may jointly form a hydroxy-protecting group; p is 0 or 1 to 3; q is 0 or 1 to 3; and the bond marked with a dashed line may be a single bond or a double bond); or a pharmaceutically acceptable salt thereof.

  用于促进神经生长因子形成的苯酚衍生物通式为 (Ia) 或 (Ib) 其中 每个 R¹ 是氢或羟基保护基团；或者 R² 是烷基、环烷基、与芳基缩合的环烷基、芳基、芳烷基或杂环基；以及 R³ 是氢或基团 R²； 或 R² 和 R³，连同它们所连接的氮原子，代表一个环状氨基； m 是 1 至 6； n 为 1 至 3，但当 n 为 2 或 3 时，两个相邻基团 R¹ 可共同形成羟基保护基团； p 为 0 或 1 至 3 q 为 0 或 1 至 3；以及 标有虚线的键可以是单键或双键）；或其药学上可接受的盐。
• KENNEDY, MICHAEL;MCKERVEY, M. ANTHONY;MAGUIRE, ANITA R.;TULADHAR, SARBAJN+, J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 1047-1054
  作者：KENNEDY, MICHAEL、MCKERVEY, M. ANTHONY、MAGUIRE, ANITA R.、TULADHAR, SARBAJN+

  DOI：——

  日期：——