2-ethenylidene-1-cyclohexanol | 50994-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethenylidene-1-cyclohexanol
• 英文别名: 2-ethenylidenecyclohexanol；2-Vinylidencyclohexanol
• CAS: 50994-80-4
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: FDKSHDJICFZWFX-UHFFFAOYSA-N

物化性质

• 沸点：
  202.9±8.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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-ethenylidene-1-cyclohexanol 在 咪唑 、 二(3-甲基丁烷-2-基)硼烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.08h， 生成
  参考文献：
  名称：

  异戊二烯的立体发散氢硼化

  摘要：

  报告了烯丙基的立体发散氢硼化的全部细节。用9-BBN对烯丙基进行硼氢化处理可在氧化后提供热力学稳定的（E）-烯丙基醇，而相同的烯丙基与HB（Sia）2（二亚氨基硼烷）的反应则形成了（Z）-烯丙基醇。动力学产物。发达的条件允许以高度立体选择性的方式合成三取代的烯烃，这被认为是具有挑战性的。该方法还用于结构基序的立体发散合成，例如跳过的二烯和烯丙基苯通常嵌入生物活性天然产物中。

  DOI：

  10.1002/asia.201800134
• 作为产物：
  描述：

  2H-吡喃,2-(6-庚炔-1-氧基)四氢 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 23.5h， 生成 2-ethenylidene-1-cyclohexanol
  参考文献：
  名称：

  Formal Synthesis of d-myo-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol

  摘要：

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).

  DOI：

  10.1021/jo990086i

文献信息

• Diastereoselective syn or anti opening of propargylic epoxides. Synthesis of α-allenic alcohols
  作者：A. Alexakis、I. Marek、P. Mangeney、J.F. Normant

  DOI：10.1016/s0040-4020(01)96911-x

  日期：1991.1

  Propargylic epoxides easily react with Grignard reagents and catalytic amounts of copper(I) salt to afford α-allenic alcohols. The reaction is highly diastereoselective and its stereochemical outcome ( or isomer) can be fully controlled. The diastereomer, probably arising through an addition-elimination mechanism, is better obtained with RMgCl and copper(I) bromide, whereas the diastereomer, is better

  炔丙基环氧化物容易与格氏试剂和催化量的铜（I）盐反应生成α-烯丙醇。该反应是高度非对映选择性的，其立体化学结果（或异构体）可以得到完全控制。使用RMgCl和溴化铜（I）可以更好地获得可能是通过加成消除机理产生的非对映异构体，而使用RMgBr和络合的铜（I）盐可以更好地获得非对映异构体。苯乙炔基环己烯氧化物与RLi和催化量的铜盐通过还原性锂离子反应，提供立体选择性的烯丙基锂试剂。
• Synthesis of allenic alcohols
  作者：Paul R. Ortiz de Montellano

  DOI：10.1039/c39730000709

  日期：——

  α-Hydroxyallenes are formed by the reaction of alkylcopper reagents with α-acetylenic epoxides.

  α-羟基丙二烯是通过烷基铜试剂与α-炔属环氧化物的反应而形成的。
• Formal Synthesis of <scp>d</scp>-<i>myo</i>-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol
  作者：Derrick L. J. Clive、Xiao He、Maarten H. D. Postema、M. Jeffrey Mashimbye

  DOI：10.1021/jo990086i

  日期：1999.6.1

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).
• Stereodivergent Hydroboration of Allenes
  作者：Yoshiyuki Nagashima、Keiji Sasaki、Takahiro Suto、Takaaki Sato、Noritaka Chida

  DOI：10.1002/asia.201800134

  日期：2018.4.16

  Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9‐BBN provided a thermodynamically stable (E)‐allylic alcohol after oxidative work‐up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)‐allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly

  报告了烯丙基的立体发散氢硼化的全部细节。用9-BBN对烯丙基进行硼氢化处理可在氧化后提供热力学稳定的（E）-烯丙基醇，而相同的烯丙基与HB（Sia）2（二亚氨基硼烷）的反应则形成了（Z）-烯丙基醇。动力学产物。发达的条件允许以高度立体选择性的方式合成三取代的烯烃，这被认为是具有挑战性的。该方法还用于结构基序的立体发散合成，例如跳过的二烯和烯丙基苯通常嵌入生物活性天然产物中。