3-cyclohexylideneprop-2-en-1-ol | 56037-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyclohexylideneprop-2-en-1-ol
• 英文别名: 3-cyclohexylidene-2-propen-1-ol
• CAS: 56037-79-7
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: DGTRYDKHEUOWHG-UHFFFAOYSA-N

物化性质

• 沸点：
  223.5±8.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3-cyclohexylideneprop-2-en-1-ol 在 di(rhodium)tetracarbonyl dichloride 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 69.0h， 生成 5-cyclohexylidene-4-methylene-1-tosyl-2,3,4,5-tetrahydro-1H-azepine
  参考文献：
  名称：

  Observation of New Cycloisomerization Pattern of 1,5-Bisallenes. Catalyst and Substituent Effects

  摘要：

  In this paper a new cycloisomerization pattern of 1,5-bisallenes based on the catalyst and substituent effects has been reported. A range of seven-membered cross-conjugated trienes 7 would be obtained efficiently via the beta-H elimination and reductive elimination of the intermediates formed via cycloisomerization.

  DOI：

  10.1021/ol070632r
• 作为产物：
  描述：

  3-(1-chlorocyclohexyl)prop-2-yn-1-ol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 3-cyclohexylideneprop-2-en-1-ol
  参考文献：
  名称：

  Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes

  摘要：

  Treatment of carbonates of alka-2,3-dien-1-ols 2 with (eta(2)-propene)Ti(O-i-Pr)(2) (I) resulted in oxidative addition to afford 1,3-dien-2-yltitanium compounds 3, which react readily with electrophiles such as H+, I-2 and aldehydes. The reaction with H+ and I-2 proceeds highly regioselectively, thus providing an efficient and practical method for synthesis of 1,3-dienes and 2-iodo-1,3-dienes. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02126-0

文献信息

• A versatile method for the preparation of allenic alcohols
  作者：Gary E. Keck、R.R. Webb

  DOI：10.1016/s0040-4039(00)87530-9

  日期：1982.1

  A convenient three step procedure to a variety of allenic alcohols is described, which relies on a highly unusual partitioning between two reaction pathways depending on the mode of addition of a reagent.

  描述了一种方便的用于多种烯丙醇的三步法，其依赖于两种反应途径之间高度不寻常的分配，这取决于试剂的添加方式。
• Metal-Triflate-Catalyzed Synthesis of Polycyclic Tertiary Alcohols by Cyclization of γ-Allenic Ketones
  作者：Ilhem Diaf、Gilles Lemière、Elisabet Duñach

  DOI：10.1002/anie.201310724

  日期：2014.4.14

  It has been established that bismuth(III) triflate catalyzes the cyclization of γ‐allenic ketones under mild reaction conditions. This reaction allows the selective formation of polycyclic tertiary alcohols from cyclic ketone derivatives. The resulting dienols can engage in stereoselective cycloadditions to efficiently afford complex polycyclic systems.

  现已确定，在温和的反应条件下，三氟甲磺酸铋（III）可以催化γ-烯烃酮的环化反应。该反应允许由环酮衍生物选择性地形成多环叔醇。所得二烯醇可以参与立体选择性环加成反应，以有效地提供复杂的多环系统。
• TfOH- and HBF₄-Mediated Formal Cycloisomerizations and [4+3] Cycloadditions of Allene-alkynylbenzenes
  作者：Yu Xiang、Zining Li、Lu-Ning Wang、Zhi-Xiang Yu

  DOI：10.1021/acs.joc.8b00393

  日期：2018.8.3

  prepared allene-alkynylbenzenes to give pyrrolidines and cyclopentanes derivatives was developed. This reaction is initiated by the generation of allylic cation from allene, followed by alkyne’s reaction with the allylic cation, to give a vinyl cation, which is finally intercepted by the triflate (TfO) anion. This cycloisomerization can be further tuned to become an acid-mediated intramolecular formal

  开发了无金属，TfOH（1.1当量）介导的易于制备的烯丙基-炔基苯的正式环异构化反应，得到吡咯烷和环戊烷衍生物。该反应通过从丙二烯生成烯丙基阳离子开始，然后由炔烃与烯丙基阳离子反应，得到乙烯基阳离子，该乙烯基阳离子最终被三氟甲磺酸根（TfO）阴离子拦截。通过使用10当量的TfOH（可以将过量的酸用于促进酸介导的环异构化产物的Friedel-Crafts反应），可以将该环异构化进一步调整为酸介导的分子内形式的[4 + 3]环加成反应。通过使用HBF 4或Me 3 OBF 4作为氟源，本系统还可以应用于合成的掺入F的产物。
• Regioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand
  作者：Josephine Eshon、Clark R. Landis、Jennifer M. Schomaker

  DOI：10.1021/acs.joc.7b01140

  日期：2017.9.15

  The efficient hydroformylation of 1,1,3-trisubstituted allenes is accomplished with low loadings of a Rh catalyst supported by a BisDiazaPhos (BDP) ligand. The ligand identity is key to achieving high regioselectivity, while the mild reaction conditions minimize competing isomerization and hydrogenation to produce β,γ-unsaturated aldehydes and their derivatives in excellent yields.

  1,2,1,3-三取代烯的有效加氢甲酰基化反应是由低负载的BisDiazaPhos（BDP）配体负载的Rh催化剂完成的。配体的同一性是实现高区域选择性的关键，而温和的反应条件可最大程度地减少竞争性异构化和氢化反应，从而以极佳的收率生产β，γ-不饱和醛及其衍生物。
• Borylative Cyclization of 1,6-Allenynes Driven by BCl₃
  作者：Chun-Hua Yang、Xiangkun Sun、Congcong Niu、Zhiwei Zhang、Mingzhu Liu、Fangjie Zheng、Ling Jiang、Xiangtao Kong、Zhantao Yang

  DOI：10.1021/acs.orglett.1c03062

  日期：2021.10.15

  A metal-free intramolecular borylative cyclization of 1,6-allenynes driven by BCl3 was developed. This method provides a general and practical strategy to construct valuable pyrrolidines containing all-carbon quaternary centers or 3,5-dihydroazepine derivatives depending on the substituents of the allene, with conjugative and sterically hindered phenyl groups favoring the latter.

  开发了由 BCl 3驱动的 1,6-丙炔的无金属分子内硼酸化环化。该方法提供了一种通用且实用的策略来构建有价值的吡咯烷，这些吡咯烷包含全碳季中心或 3,5-二氢吖庚因衍生物，具体取决于丙二烯的取代基，共轭和空间位阻苯基有利于后者。