2-Methoxycarbonylmethyl-7-methyl-1-oxo-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester | 189091-61-0

• 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-Methoxycarbonylmethyl-7-methyl-1-oxo-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester
• 英文别名: methyl 2-(2-methoxy-2-oxoethyl)-4-methyl-3-oxo-4,5,6,7-tetrahydro-1H-indene-2-carboxylate
• CAS: 189091-61-0
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: JFRMOWVIVSXQJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-Methoxycarbonylmethyl-7-methyl-1-oxo-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester 在 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 溶剂黄146 为溶剂， 生成 (3aR,8S,8bR)-8-Methyl-3,3a,4,5,6,7,8,8b-octahydro-indeno[1,2-b]furan-2-one
  参考文献：
  名称：

  Synthesis of All Eight Stereoisomers of the Germination Stimulant Sorgolactone

  摘要：

  The naturally occurring sesquiterpene sorgolactone (2) belongs to the class of "strigolactones", which are highly potent germination stimulants for seeds of the parasitic weeds Striga and Orobanche. The aim of the present work was to synthesize all eight stereoisomers of sorgolactone and to evaluate their activities in the stimulation of germination of S. hermontica and O. crenata. Two racemic diastereomers of the ABC part of sorgolactone, rac.10a and rac.10b respectively, were prepared and coupled with homochiral latent D-ring synthons 12 and ent.12. In this manner, four mixtures of two separable (protected) sorgolactone diastereomers were obtained. Deprotection gave all eight target compounds as single isomers. Bioassays revealed that only those isomers possessing the same stereochemistry as natural sorgolactone at two adjacent chiral centers exhibit high biological activities.

  DOI：

  10.1021/jo9718408
• 作为产物：
  描述：

  7-methyl-2,3,4,5,6,7-hexahydro-inden-1-one 在 sodium hydride 作用下， 生成 2-Methoxycarbonylmethyl-7-methyl-1-oxo-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  天然发芽兴奋剂高粱内酯的第一个全合成

  摘要：

  报道了高粱内酯的第一个全合成，证实了自然萌发刺激物的拟议结构。

  DOI：

  10.1016/s0040-4039(97)00304-3

文献信息

• The first total synthesis of the naturally occurring germination stimulant sorgolactone
  作者：Yukihiro Sugimoto、Suzanne C.M. Wigchert、Jan Willem J.F. Thuring、Binne Zwanenburg

  DOI：10.1016/s0040-4039(97)00304-3

  日期：1997.3

  The first total synthesis of sorgolactone is reported, which confirms the proposed structure of the naturally occurring germination stimulant.

  报道了高粱内酯的第一个全合成，证实了自然萌发刺激物的拟议结构。
• Synthesis of All Eight Stereoisomers of the Germination Stimulant Sorgolactone
  作者：Yukihiro Sugimoto、Suzanne C. M. Wigchert、Jan Willem J. F. Thuring、Binne Zwanenburg

  DOI：10.1021/jo9718408

  日期：1998.2.1

  The naturally occurring sesquiterpene sorgolactone (2) belongs to the class of "strigolactones", which are highly potent germination stimulants for seeds of the parasitic weeds Striga and Orobanche. The aim of the present work was to synthesize all eight stereoisomers of sorgolactone and to evaluate their activities in the stimulation of germination of S. hermontica and O. crenata. Two racemic diastereomers of the ABC part of sorgolactone, rac.10a and rac.10b respectively, were prepared and coupled with homochiral latent D-ring synthons 12 and ent.12. In this manner, four mixtures of two separable (protected) sorgolactone diastereomers were obtained. Deprotection gave all eight target compounds as single isomers. Bioassays revealed that only those isomers possessing the same stereochemistry as natural sorgolactone at two adjacent chiral centers exhibit high biological activities.