2-(1-Cyclohexenyl)-3-buten-2-ol | 152589-38-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-Cyclohexenyl)-3-buten-2-ol
• 英文别名: 2-(Cyclohexen-1-yl)but-3-en-2-ol
• CAS: 152589-38-3
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: IYXCFQCUWKCAFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2-(1-Cyclohexenyl)-3-buten-2-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 四氯化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 2-Acetyl-2-ethenylcyclohexan-1-ol
  参考文献：
  名称：

  Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms

  摘要：

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.

  DOI：

  10.1021/jo00074a019
• 作为产物：
  描述：

  乙烯基溴化镁 、 乙酰基环已烯 以 四氢呋喃 为溶剂， 生成 2-(1-Cyclohexenyl)-3-buten-2-ol
  参考文献：
  名称：

  Calyciphylline A 型生物碱 (−)-10-Deoxydaphnipaxianine A、(+)-Daphlongamine E 和 (+)-Calyciphylline R 通过后期二乙烯醇重排的全合成

  摘要：

  在著名的Daphniphyllum生物碱家族中，花萼碱 A 型亚家族近年来引起了有机合成界的特别兴趣。在这里，我们报告了三种花萼碱 A 型生物碱的不同总合成，即 (−)-10-deoxydaphnipaxianine A、(+)-daphlongamine E 和 (+)-calyciphylline R。我们的工作通过以下方式突出了一种有效的、不同的策略后期二乙烯醇重排，包括使用未官能化的叔二乙烯醇和不寻常的烯丙醇重排进行的前所未有的氧化纳扎罗夫电环化。一种高效的“供体-受体”铂催化剂用于关键的腈水合步骤。此外，选择性酰胺还原的力量也通过新颖和经典的策略得到了展示。

  DOI：

  10.1021/jacs.2c05957

文献信息

• Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols
  作者：James M. Takacs、Xun-tian Jiang、Alexei P. Leonov

  DOI：10.1016/s1268-7731(03)00074-2

  日期：2003.9

  The triethylborane-promoted and palladium-catalyzed reactions of 2,4-dienyl alcohols or the corresponding isomeric divinyl alcohols with bis(trifluoroethyl) malonates provide an improved method for the regio- and stereoselective dienylation of malonates. The phosphine ligand is an important control element in the reaction. Combinations of Pd(OAc)(2) with BIPHEP or BINAP give dienylated malonates in good yield and higher isomeric purity than the traditional combination of Pd(OAc)(2) and Ph3P affords in the catalyzed reactions of dienyl acetates. (C) 2003 Elsevier Ltd. All rights reserved.
• Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms
  作者：Charles M. Marson、Andrew J. Walker、Jane Pickering、Adrian D. Hobson、Roger Wrigglesworth、Simon J. Edge

  DOI：10.1021/jo00074a019

  日期：1993.10

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.
• Total Syntheses of Calyciphylline A-Type Alkaloids (−)-10-Deoxydaphnipaxianine A, (+)-Daphlongamine E and (+)-Calyciphylline R via Late-Stage Divinyl Carbinol Rearrangements
  作者：Yan Zhang、Yuye Chen、Manrong Song、Bin Tan、Yujia Jiang、Chongyuan Yan、Yuyang Jiang、Xinyue Hu、Chengqian Zhang、Wenqing Chen、Jing Xu

  DOI：10.1021/jacs.2c05957

  日期：2022.9.7

  A-type subfamily has triggered particular interest from the organic synthesis community in recent years. Here, we report divergent total syntheses of three calyciphylline A-type alkaloids, namely, (−)-10-deoxydaphnipaxianine A, (+)-daphlongamine E, and (+)-calyciphylline R. Our work highlights an efficient, divergent strategy via late-stage divinyl carbinol rearrangements, including an unprecedented oxidative

  在著名的Daphniphyllum生物碱家族中，花萼碱 A 型亚家族近年来引起了有机合成界的特别兴趣。在这里，我们报告了三种花萼碱 A 型生物碱的不同总合成，即 (−)-10-deoxydaphnipaxianine A、(+)-daphlongamine E 和 (+)-calyciphylline R。我们的工作通过以下方式突出了一种有效的、不同的策略后期二乙烯醇重排，包括使用未官能化的叔二乙烯醇和不寻常的烯丙醇重排进行的前所未有的氧化纳扎罗夫电环化。一种高效的“供体-受体”铂催化剂用于关键的腈水合步骤。此外，选择性酰胺还原的力量也通过新颖和经典的策略得到了展示。