trans-2-methyloctahydrobenzofuran | 23204-77-5

• 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-2-methyloctahydrobenzofuran
• 英文别名: (rac-3aR,2R,7aS)-2-methyloctahydrobenzofuran；3a,7a-trans-2-methyloctahydrobenzofuran；(2S,3aR,7aS)-2-methyl-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran
• CAS: 23204-77-5；23204-78-6；29183-69-5；55697-85-3；59958-44-0；110575-15-0；110575-16-1；110575-17-2；110575-18-3
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: VCHIIUXIMFPSKT-YIZRAAEISA-N

物化性质

• 沸点：
  75 °C(Press: 17 Torr)
• 密度：
  0.931 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反-2-(丙-2-烯-1-基)环己烷-1-醇 在 碘 、 三苯基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 cis-2-methyloctahydrobenzofuran 、 trans-2-methyloctahydrobenzofuran
  参考文献：
  名称：

  Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System

  摘要：

  A novel catalytic system using I-2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

  DOI：

  10.1021/acs.orglett.5b01797

文献信息

• Iodocyclization of 2-allylcyclohexanols
  作者：Yu. I. Gevaza、I. P. Kupchik、V. I. Staninets、V. N. Kalinin、A. G. Bratolyubova

  DOI：10.1007/bf00504193

  日期：1985.2
• Reductive and Brominative Termination of Alkenol Cyclization in Aerobic Cobalt-Catalyzed Reactions
  作者：Dominik Schuch、Patrick Fries、Maike Dönges、Bárbara Menéndez Pérez、Jens Hartung

  DOI：10.1021/ja904577c

  日期：2009.9.16

  Tetrahydrofur-2-ylmethyl radicals were stereoselectively generated from substituted pent-4-en-1-ols in aerobic cobalt(II)-catalyzed oxidations. Intermediates were trapped with cyclohexa-1,4-diene, gamma-terpinene, BrCCl3, diethyl dibromomalonate, or electron-deficient olefins such as acrylonitrile or dimethyl fumarate to afford functionalized tetrahydrofurans in synthetically useful yields.
• Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System
  作者：Shoji Fujita、Masanori Abe、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1021/acs.orglett.5b01797

  日期：2015.8.7

  A novel catalytic system using I-2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.