trans-hexahydro-3-benzylidene-2(3H)-benzofuranone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: trans-hexahydro-3-benzylidene-2(3H)-benzofuranone
• 英文别名: (3E,3aS,7aR)-3-benzylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: NKQRCKBRNIYLNM-BILBVFMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  S-methyl O-trans-2-phenylethynylcyclohexyl dithiocarbonate 在 盐酸 、 三乙基硼 、 三正丁基氢锡 作用下， 以 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 0.5h， 生成 trans-hexahydro-3-benzylidene-2(3H)-benzofuranone
  参考文献：
  名称：

  用 n-Bu3SnH-Et3B 轻松还原仲醇衍生的二硫代碳酸酯，并通过烷氧基硫代羰基自由基与乙炔键的分子内加成合成 2-呋喃硫酮和 2-呋喃酮

  摘要：

  n-Bu3SnH–Et3B 还原二硫代碳酸盐或硫代碳酸盐很容易得到相应的碳氢化合物。中间体烷氧基硫代羰基自由基等价物被适当定位的碳-碳多重键捕获。衍生自高炔丙醇或高烯丙醇的二硫代碳酸酯在用 n-Bu3SnH–Et3B 处理后产生四氢呋喃酮。还描述了这种新方法在将羰基化合物转化为烯烃中的应用。

  DOI：

  10.1246/bcsj.63.2578

文献信息

• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.
• Synthesis of lactones by intramolecular addition of alkoxythiocarbonyl free radicals to acetylenes
  作者：Kyoko Nozaki、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(00)82284-4

  日期：——
• Conformational effects on lipase-mediated acylations of 2-substituted cyclohexanols
  作者：Rikuhei Tanikaga、Yoshimasa Matsumoto、Maki Sakaguchi、Yohei Koyama、Kentaro Ono

  DOI：10.1016/s0040-4039(03)01514-4

  日期：2003.8

  Lipase-mediated acetylations of trans- and cis-2-substituted cyclohexanols gave the corresponding (1R)-cyclohexyl acetates and (IS)-cyclohexanols in high yields and ee, but c-4-tert-butyl-c-2-ethenyl-r-l-cyclohexanoI was unreactive owing to the steric interaction between the axial OH group and the axial H atoms at the 3- and 5-positions. In the cis-isomer the OH group occupies an equatorial position to bind to the lipase, and less bulky axial alkenyl and alkynyl groups might not so much prevent acetylations than an alkyl group. (C) 2003 Elsevier Ltd. All rights reserved.