(R)-2,4,4-trimethyl-3-vinyl-2-cyclohexene-1-ol | 123286-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2,4,4-trimethyl-3-vinyl-2-cyclohexene-1-ol
• 英文别名: (R)-2,4,4-trimethyl-3-vinyl-cyclohex-2-enol；(1R)-3-ethenyl-2,4,4-trimethylcyclohex-2-en-1-ol
• CAS: 123286-37-3
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: YHJHVPJJBQAHFZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2,4,4-trimethyl-3-vinyl-2-cyclohexene-1-ol 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 (8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-3,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 1(R)-hydroxypolygodial

  摘要：

  Enantioselective preparation of 1(R)-hydroxypolygodial (5) has been achieved starting from alpha-ionone through a synthetic strategy involving a Corey-Bakshi-Shibata oxazaborolidine-mediated reduction and a stereoselective Diels-Alder reaction as key steps. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.020
• 作为产物：
  描述：

  2,3-epoxy-2,6,6-trimethylcyclohexane-1-carboxaldehyde 在 四氢吡咯 、 重铬酸吡啶 、 正丁基锂 、 硼烷四氢呋喃络合物 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (R)-2,4,4-trimethyl-3-vinyl-2-cyclohexene-1-ol
  参考文献：
  名称：

  Enantioselective synthesis of 1(R)-hydroxypolygodial

  摘要：

  Enantioselective preparation of 1(R)-hydroxypolygodial (5) has been achieved starting from alpha-ionone through a synthetic strategy involving a Corey-Bakshi-Shibata oxazaborolidine-mediated reduction and a stereoselective Diels-Alder reaction as key steps. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.020

文献信息

• The first enantioselective total synthesis of (−)-arisugacin A
  作者：Kevin P. Cole、Richard P. Hsung

  DOI：10.1016/s0040-4039(02)02094-4

  日期：2002.11

  The first enantioselective synthesis of (−)-arisugacin A in 17 steps is described here, featuring a CBS asymmetric ketone reduction and a highly stereoselective formal [3+3] cycloaddition approach. This concise synthesis of the enantiomer unambiguously confirms the original assignment of the absolute configuration.

  本文描述了17个步骤中（-）-瑞新霉素A的首次对映选择性合成，其特征在于CBS不对称酮还原和高度立体选择性的形式[3 + 3]环加成方法。对映异构体的这种简明合成清楚地证实了绝对构型的原始分配。
• Enantioselective route to a key intermediate in the total synthesis of forskolin
  作者：E.J. Corey、Paul Da Silva Jardine、Tetsuya Mohri

  DOI：10.1016/s0040-4039(00)82359-x

  日期：1988.1

  An enantioselective route for the total synthesis of forskolin, a potent activator of adenylate cyclase, has been developed which is based on reduction of dienone 3 to the (S)-alcohol 4 and conversion in two steps to tricyclic lactone 9, obtained in optically pure form simply by recrystallization.

  已经开发了一种用于全合成福斯高林的对映体选择性路线，这是一种有效的腺苷酸环化酶激活剂，它基于将二烯酮3还原为（S）-醇4并分两步转化为光学纯的三环内酯9的方法。只需通过重结晶即可形成。
• Enantioselective Total Syntheses of Cassane Furanoditerpenoids and Their Stimulation of Cellular Respiration in Brown Adipocytes
  作者：Hendrik H. Bulthaupt、Fabian Glatz、Sven M. Papidocha、Chunyan Wu、Shawn Teh、Susanne Wolfrum、Lucia Balážová、Christian Wolfrum、Erick M. Carreira

  DOI：10.1021/jacs.3c07597

  日期：2023.10.4

  We report the first and enantioselective total syntheses of (+)-1-deacetylcaesalmin C, (+)-δ-caesalpin, (+)-norcaesalpinin MC, and (+)-norcaesalpinin P. Salient features of the synthetic strategy are an exo-selective intramolecular Diels–Alder reaction of a furanoquinone monoketal and subsequent chemoselective reduction of the resulting pentacyclic furfuryl ketal, furnishing a keystone intermediate

  我们报告了 (+)-1-de乙酰caesalmin C、(+)-δ-caesalpin、(+)-norcaesalpinin MC 和 (+)-norcaesalpinin P 的首次对映选择性全合成。合成策略的显着特征是外切-呋喃醌单缩酮的选择性分子内狄尔斯-阿尔德反应，随后对所得五环糠基缩酮进行化学选择性还原，提供关键中间体。后者可以通过实施立体选择性氧化来收集天然产物。在获得了卡桑呋喃二萜类化合物后，我们揭示了以前未知的生物活性：(+)-1-脱乙酰凯撒明 C 刺激棕色脂肪细胞的呼吸，这被认为在肥胖治疗中发挥着核心作用。
• Enantioselective synthesis of 1-(R)-hydroxypolygodial and its 9α epimer, 1-(R)-hydroxyisotadeonal
  作者：Carmela Della Monica、Giorgio Della Sala、Irene Izzo、Luciano De Petrocellis、Vincenzo di Marzo、Aldo Spinella

  DOI：10.1016/j.tet.2007.04.059

  日期：2007.7

  The enantioselective synthesis of 1-(R)-hydroxypolygodial and its epimer at C-9 is described. alpha-Ionone was the starting material. Key steps of these syntheses included a Corey-Bakshi-Shibata oxazaborolidine-mediated reduction and a stereoselective Diels-Alder reaction. No vanilloid activity was detected for both compounds in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1. (c) 2007 Elsevier Ltd. All rights reserved.
• A synthesis of an optically active forskolin intermediate via allenyl ether intramolecular cycloaddition strategy
  作者：Shigeu Nagashima、Ken Kanematsu

  DOI：10.1016/s0957-4166(00)82387-3

  日期：1990.1