(6-methyl-1,3-dihydroisobenzofuran-5-yl)methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (6-methyl-1,3-dihydroisobenzofuran-5-yl)methanol
• 英文别名: (6-Methyl-1,3-dihydroisobenzofuran-5-yl)methanol；(6-methyl-1,3-dihydro-2-benzofuran-5-yl)methanol
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: OGGHNQUXFGVBEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6-methyl-1,3-dihydroisobenzofuran-5-yl)methanol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以61%的产率得到5-(chloromethyl)-6-methyl-1,3-dihydro-2-benzofuran
  参考文献：
  名称：

  SITAXENTAN DERIVATIVE

  摘要：

  式（1-1）或（1-2）所代表的化合物，或其药学上可接受的盐，保留了西他昔单的主要治疗效果，并具有改善的CYP抑制效果：其中R1是卤素原子等，R2是甲基基团等，R3是C1-6烷基基团等，M是由以下代表的基团：等。

  公开号：

  US20130197045A1
• 作为产物：
  描述：

  四溴甲苯 在 4,4'-二叔丁基苯并 、 四丁基氢氧化铵 、 水 、 lithium 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 (6-methyl-1,3-dihydroisobenzofuran-5-yl)methanol
  参考文献：
  名称：

  SITAXENTAN DERIVATIVE

  摘要：

  式（1-1）或（1-2）所代表的化合物，或其药学上可接受的盐，保留了西他昔单的主要治疗效果，并具有改善的CYP抑制效果：其中R1是卤素原子等，R2是甲基基团等，R3是C1-6烷基基团等，M是由以下代表的基团：等。

  公开号：

  US20130197045A1

文献信息

• Practical Solvent-Free Ruthenium Trichloride-Mediated Benzannulation Approach to Fused Functionalized Arenes
  作者：Jeremy Jacquet、Anne-Laure Auvinet、Anil Kumar Mandadapu、Mansour Haddad、Virginie Ratovelomanana-Vidal、Véronique Michelet

  DOI：10.1002/adsc.201500186

  日期：2015.5.4

  The solvent‐ and ligand‐free [2+2+2] ruthenium‐promoted cycloaddition of α,ω‐diynes and alkynes provides a facile and efficient strategy for the synthesis of substituted benzene‐derived systems. The search for the optimal reaction conditions revealed the unprecedented catalytic activity of ruthenium trichloride for benzannulation reactions and this atom‐economical process allowed the synthesis of fused

  无溶剂和无配体的[2 + 2 + 2]钌促进的α，ω-二炔和炔烃的环加成反应为合成取代苯衍生的体系提供了便捷而有效的策略。对最佳反应条件的探索揭示了三氯化钌对苯环化反应具有空前的催化活性，并且这种原子经济的过程允许以高产率高收率地合成包括二氢苯并呋喃，异吲哚啉，茚满的稠合芳烃。该实用方案还引发了五取代芳族衍生物的制备，并被用于功能化杂环的1克级合成。
• Sitaxentan derivative
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US08592470B2

  公开（公告）日：2013-11-26

  A compound represented by formula (1-1) or (1-2), or a pharmacologically acceptable salt thereof retains the principal therapeutic effect of sitaxentan and has an improved CYP inhibitory effect: wherein R1 is a halogen atom, etc., R2 is a methyl group, etc., R3 is a C1-6 alkyl group, etc., and M is a group represented by: etc.

  化合物由式（1-1）或（1-2）表示，或其药学上可接受的盐，保留了西他昔单的主要治疗效果，并具有改善的CYP抑制作用：其中R1为卤素原子等，R2为甲基基团等，R3为C1-6烷基基团等，M为由以下表示的基团：等。
• SITAXSENTAN DERIVATIVE
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2810943A1

  公开（公告）日：2014-12-10

  A compound represented by formula (1-1) or (1-2), or a pharmacologically acceptable salt thereof retains a principal therapeutic effect of sitaxentan and has an improved CYP inhibitory effect. wherein R1 is a halogen atom, etc., R2 is a methyl group, etc., R3 is a C1-6 alkyl group, etc., and M is a group represented by: etc.

  由式（1-1）或（1-2）代表的化合物或其药理上可接受的盐保留了西他森坦的主要治疗效果，并具有更好的 CYP 抑制作用。 其中 R1 是卤素原子等，R2 是甲基等，R3 是 C1-6 烷基等，M 是由以下各项代表的基团： 等代表的基团。
• Regioselective reductive opening of substituted phthalans: synthetic applications
  作者：Daniel García、Francisco Foubelo、Miguel Yus

  DOI：10.1016/j.tet.2008.02.072

  日期：2008.5

  The reductive opening of substituted phthalans 6, 11, 12, 20, 21 and 28 with lithium and a catalytic amount of DTBB leads to the formation of corresponding functionalised organolithium intermediates 8, 15, 16, 23, 25 and 29+30 in a regioselective manner. The further reaction of these dianions with different electrophiles, mainly carbonyl compounds, gives the expected functionalised benzylic alcohols 9, 17, 18, 24, 26 and 31+32. The observed stereochemistry can be easily explained taking into account the values of the electron densities deduced by semiempirical PM3 calculations. (c) 2008 Elsevier Ltd. All rights reserved.
• Regiochemistry in the reductive opening of phthalan derivatives
  作者：Francisco Foubelo、Daniel García、Benjamín Moreno、Miguel Yus

  DOI：10.1016/j.tetlet.2007.03.069

  日期：2007.5

  The lithiation of phthalan derivatives 4, 9 and 12 with an excess of lithium in the presence of a catalytic amount of 4,4'-ditert-butylbiphenyl (DTBB) in THF at -78 degrees C gives dianionic intermediates 5, 10 and 13, respectively, which by reaction with different electrophiles [H2O, tau-BuCHO, Me2CO, (EtO)(2)CO] at the same temperature, followed by hydrolysis, leads to regioselective functionalised naphthalenes 7, and biphenyls 11 and 14. The reductive opening takes place with high or total regioselectivity and can be explained considering the electron density in the dianion or in the radical anion, which are formed previous to the carbon-oxygen bond excision. The lithiation of the dihydrofurophthalan derivative 18 with the same reaction mixture but at higher temperature (0 degrees C) leads to intermediates 19 and 20, resulting from a single and a double reductive cleavage, respectively, which after addition of H2O and benzaldehyde as electrophiles gives a mixture of compounds 21 and 22. (c) 2007 Elsevier Ltd. All rights reserved.