2-acetylmethyl-2,7-dimethyl-7-carbomethoxybicyclo[3.3.0]octan-3-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-acetylmethyl-2,7-dimethyl-7-carbomethoxybicyclo[3.3.0]octan-3-one
• 英文别名: methyl (2S,3aR,6S,6aR)-2,6-dimethyl-5-oxo-6-(2-oxopropyl)-3,3a,4,6a-tetrahydro-1H-pentalene-2-carboxylate
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: LUEKDXDDBYUOSS-JLUCKKNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetylmethyl-2,7-dimethyl-7-carbomethoxybicyclo[3.3.0]octan-3-one 以79%的产率得到
  参考文献：
  名称：

  NISHIDA, MAYUMI;ISEKI, KATSUHIKO;SHIBASAKI, MASAKATSU;IKEGAMI, SHIRO, CHEM. AND PHARM. BULL., 38,(1990) N2, C. 3230-3237

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3aS,4R,6aS)-2,4-Dimethyl-5-oxo-octahydro-pentalene-2-carbaldehyde 在 sodium hydride 、 palladium dichloride 作用下， 以 乙二醇二甲醚 为溶剂， 生成 2-acetylmethyl-2,7-dimethyl-7-carbomethoxybicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  顺式-双环[3.3.O]OCTAN-2-ONE到其3-ONE骨架的1,2-羰基转位：在dl-多毛酸和dl-9(0)-甲基前列腺环素合成中的应用

  摘要：

  描述了 dl-毛草酸的合成路线和 dl-9(0)-methanoprostacyclin 的改进合成，这两种方法均采用 1,2-羰基转座作为关键步骤。

  DOI：

  10.1246/cl.1981.1245

文献信息

• A short formal total synthesis of (±)-hirsutic acid
  作者：Guillaume Revol、Christian Fuchs、Samir Z. Zard

  DOI：10.1139/v2012-037

  日期：2012.11

  A short formal total synthesis of (±)-hirsutic acid is described using a Claisen rearrangement and a radical cascade as the key steps. The radical sequence involves an intermolecular addition of a radical derived from a xanthate followed by a cyclization and transfer of the xanthate group.

  本文介绍了一种简短的正式全合成(±)-hirsutic acid的方法，其中Claisen重排和自由基级联反应是关键步骤。自由基序列包括从黄酸酯中衍生出的自由基的分子间加成，随后进行环化和黄酸酯基团的转移。
• A total synthesis of(+)-hirsutic acid.
  作者：Mayumi NISHIDA、Katsuhiko ISEKI、Masakatsu SHIBASAKI、Shiro IKEGAMI

  DOI：10.1248/cpb.38.3230

  日期：——

  The first asymmetric total synthesis of (+)-hirsutic acid has been accomplished in a highly stereocontrolled manner, including a novel method for the preparation of (1S, 5R, 6S)-6-hydroxy-cis-bicyclo[3.3.0]octan-3-one and a stereospecific Simmons-Smith reaction controlled by the participation of a relatively remote hydroxyl group.

  首次以高度立体控制的方式完成了(+)-毛木酸的不对称全合成，其中包括一种制备(1S,5R,6S)-6-羟基-顺式-双环[3.3.0]辛烷的新方法-3-酮和由相对较远的羟基参与控制的立体特异性西蒙斯-史密斯反应。
• A simple, highly stereocontrolled total synthesis of (+)-hirsutic acid
  作者：Masakatsu Shibasaki、Mayumi Yamazaki、Katsuhiko Iseki、Shiro Ikegami

  DOI：10.1016/s0040-4039(00)85826-8

  日期：——

  A chirally directed total synthesis of (+)-hirsutic acid from 1,3-cyclooctadiene has been accomplished in a highly stereocontrolled manner.

  由1,3-环辛二烯手性完全合成（+）-亚硫酸的酸已经以高度立体可控的方式完成。
• Synthesis of embellished bicyclo[2.2.2]octenones and a sigmatropic 1,2-acyl shift in an excited state: a novel and stereoselective route to (±)-hirsutic acid C and complicatic acid
  作者：Vishwakarma Singh、Dilip K. Tosh、Shaikh M. Mobin

  DOI：10.1016/j.tetlet.2003.12.095

  日期：2004.2

  Formal syntheses of hirsutic acid C and complicatic acid via cycloaddition of cyclohexa-2,4-dienone with methyl methacrylate and a triplet sensitized 1,2-acyl shift are described. The X-ray crystal structure of one of the key intermediates is also reported.

  描述了通过环己基2，4-二烯酮与甲基丙烯酸甲酯的环加成反应和三重态敏化的1，2-酰基转移而形成的水杨酸C和复杂酸的形式合成。还报道了关键中间体之一的X射线晶体结构。
• Molecular complexity from aromatics. Cycloaddition of cyclohexa-2,4-dienones, sigmatropic 1,2-acyl shift and ring-closing metathesis: a new, efficient, and stereoselective synthesis of (±)-hirsutic acid C and medium ring carbocycles
  作者：Vishwakarma Singh、Shantanu Pal、Dilip K. Tosh、Shaikh M. Mobin

  DOI：10.1016/j.tet.2007.01.006

  日期：2007.3

  A new, stereoselective formal synthesis of hirsutic acid and medium ring carbocyclic systems from salicyl alcohol is described. Cycloaddition between electron deficient partners such as cyclohexa-2,4-dienone and methylmethacrylate, triplet sensitized 1,2-acyl shift and ring-closing metathesis are the key features of our approach. (c) 2007 Elsevier Ltd. All rights reserved.