6-isoprenyl-9-methyl-5,2-oxathiospiro[4,5]decane | 518326-98-2

• 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: 6-isoprenyl-9-methyl-5,2-oxathiospiro[4,5]decane
• 英文别名: (5S,9R)-9-methyl-6-propan-2-ylidene-1-oxa-4-thiaspiro[4.5]decane
• CAS: 518326-98-2
• 化学式: C₁₂H₂₀OS
• 分子量: 212.356
• InChiKey: LZKXOIGSGBFZLX-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 6-isoprenyl-9-methyl-5,2-oxathiospiro[4,5]decane 在 四氯化钛 、 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到(R)-4,4,7-Trimethyl-2-phenyl-3,4,5,6,7,8-hexahydro-2H-thiochromene
  参考文献：
  名称：

  α,β-Unsaturated 1,3-oxathiolanes as masked heterodienes in the thio Diels–Alder reaction with styrene derivatives

  摘要：

  The cycloaddition reactions of various alkyl and aryl substituted alpha,beta-unsaturated 1,3-oxathiolanes with styrene derivatives led to dihydrothiapyrans in the presence of TiCl4. Some mechanistic aspects of the cycloaddition are presented. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02642-4
• 作为产物：
  描述：

  长叶薄荷酮 、 2-巯基乙醇 在 aminopropylated silica gel hydrochloride 、 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以53%的产率得到6-isoprenyl-9-methyl-5,2-oxathiospiro[4,5]decane
  参考文献：
  名称：

  Synthesis of α,β-unsaturated oxathiolanes

  摘要：

  The formation of alpha,beta-unsaturated oxathiolanes 2 from alpha,beta-unsaturated carbonyl derivatives was achieved selectively and in high yields using the heterogeneous catalyst APSG(.)HCI. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01428-x

文献信息

• Thio Diels–Alder reactions of α,β-unsaturated 1,3-oxathiolanes with aliphatic olefins and 1,3-dienes
  作者：Sébastien Kerverdo、Louisette Lizzani-Cuvelier、Elisabet Duñach

  DOI：10.1016/j.tetlet.2003.09.194

  日期：2003.12

  A series of α,β-unsaturated 1,3-oxathiolanes reacted with aliphatic olefins such as norbornene and with various 1,3-dienes in the presence of TiCl4 leading to dihydrothiapyrans, via a cycloaddition-type reaction. The unsaturated oxathiolanes acted as masked heterodienes in this thio Diels–Alder reaction.

  一系列α，β-不饱和的1，3-氧杂硫杂环戊烷通过环加成型反应在TiCl 4存在下与脂肪族烯烃如降冰片烯和与各种1，3-二烯反应，生成二氢噻喃。在该硫代Diels-Alder反应中，不饱和氧杂硫杂环戊烷充当掩蔽的杂二烯。
• Synthesis of α,β-unsaturated oxathiolanes
  作者：Sébastien Kerverdo、Louisette Lizzani-Cuvelier、Elisabet Duñach

  DOI：10.1016/s0040-4020(02)01428-x

  日期：2002.12

  The formation of alpha,beta-unsaturated oxathiolanes 2 from alpha,beta-unsaturated carbonyl derivatives was achieved selectively and in high yields using the heterogeneous catalyst APSG(.)HCI. (C) 2002 Elsevier Science Ltd. All rights reserved.
• α,β-Unsaturated 1,3-oxathiolanes as masked heterodienes in the thio Diels–Alder reaction with styrene derivatives
  作者：Sébastien Kerverdo、Louisette Lizzani-Cuvelier、Elisabet Duñach

  DOI：10.1016/s0040-4039(02)02642-4

  日期：2003.1

  The cycloaddition reactions of various alkyl and aryl substituted alpha,beta-unsaturated 1,3-oxathiolanes with styrene derivatives led to dihydrothiapyrans in the presence of TiCl4. Some mechanistic aspects of the cycloaddition are presented. (C) 2003 Elsevier Science Ltd. All rights reserved.