(Z)-6-phenyl-2-hexen-1-ol | 130700-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-6-phenyl-2-hexen-1-ol
• 英文别名: Z-6-phenylhex-2-en-1-ol；(Z)-6-phenylhex-2-en-1-ol
• CAS: 130700-06-0
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: TWRPBAOFAWNQQI-UQCOIBPSSA-N

物化性质

• 沸点：
  300.8±21.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-6-phenyl-2-hexen-1-ol 在 2,6-二甲基吡啶 、 甲基磺酰氯 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 以84%的产率得到Z-(6-chlorohex-4-en-1-yl)benzene
  参考文献：
  名称：

  双氢亲核氢化物的催化生成和化学选择性转移

  摘要：

  铜（I）–N-杂环卡宾（NHC）配合物能够催化从二氢（H 2）生成亲核氢化物，然后将其转移至烯丙基氯化物。具有高度化学选择性的催化剂没有显示出伴随的氢化反应性；实际上，在氢化物转移中形成的末端双键保持完整。切换到氘气（D 2）可以实现区域选择性单氘化，并具有出色的同位素掺入能力。

  DOI：

  10.1002/chem.201805530
• 作为产物：
  描述：

  6-苯基己-2-炔-1-醇 在 Lindlar catalyst 3,6-二硫杂-1,8-辛二醇 、 氢气 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (Z)-6-phenyl-2-hexen-1-ol
  参考文献：
  名称：

  铱络合物催化的烯丙酯和烯丙醇的烯丙基烷基化：独特的区域选择性和立体选择性

  摘要：

  发现铱配合物是烯丙基酯与稳定的碳亲核试剂烯丙基烷基化的有效催化剂。取代的烯丙基基团上的高度区域选择性烷基化...

  DOI：

  10.1021/ja981560p

文献信息

• Enantioselective Construction of Cyclopropane Rings via Asymmetric Simmons-Smith Reaction of Allylic Alcohols.
  作者：Yutaka Ukaji、Mitsuhiro Nishimura、Tamotsu Fujisawa

  DOI：10.1246/cl.1992.61

  日期：——

  The Simmons-Smith reaction starting from allylic alcohols using (R,R)-diethyl tartrate as a chiral auxiliary was found to proceed enantioselectively; i.e., the treatment of allylic allylic alcohols with diethylzinc and diethyl tartrate, followed by the reaction with diethylzinc and diiodomethane, afforded the corresponding cyclopropylmethyl alcohols in optically active form

  发现以 (R,R)-酒石酸二乙酯为手性助剂，以烯丙醇为原料的 Simmons-Smith 反应对映选择性进行；即，用二乙基锌和酒石酸二乙酯处理烯丙醇，然后与二乙基锌和二碘甲烷反应，得到相应的旋光形式的环丙基甲醇
• Stereoselective Carbocyclization of Vinyloxiranes Catalyzed by Lewis Acids: Construction of the Musellarin Tricyclic Core
  作者：Sehui Yang、Euijin Park、Jimin Kim

  DOI：10.1002/bkcs.12236

  日期：2021.4

  Stereoselective carbocyclizations of vinyloxiranes were efficiently catalyzed by Lewis acids to provide cyclic homoallyl alcohols as single isomers. The choice of Lewis acid, B(C6F5)3 was crucial for the stereoselective transformation in the case of cis vinyloxiranes, whereas BF3∙OEt2 was proven to be an effective catalyst for trans substrates. The method was well implemented in the synthesis of seven‐membered

  乙烯基氧杂环丁烷的立体选择性碳环化被路易斯酸有效地催化，以提供环状均烯丙基醇作为单一异构体。在顺式乙烯基环氧乙烷的情况下，路易斯酸B（C 6 F 5）3的选择对于立体选择性转化至关重要，而事实证明BF 3 ∙OEt 2是反式底物的有效催化剂。该方法在具有官能团耐受性的七元环和六元环的合成中得到了很好的实现。所得的效用反式-和顺高烯丙基醇被证明简明地建立musellarin A和E的三环核心
• Complete Retention of <i>Z</i> Geometry in Allylic Substitution Catalyzed by an Iridium Complex
  作者：Ryo Takeuchi、Norihito Shiga

  DOI：10.1021/ol990033n

  日期：1999.7.1

  [GRAPHICS]The Z geometry of methyl (Z)-3-monosubstituted-2-alkenyl carbonate was completely retained in iridium complex-catalyzed allylic amination. The reaction of methyl (Z)-2-nonenyl carbonate with piperidine in the presence of a catalytic amount of [Ir(COD)Cl](2) and P(OPh)(3) at 50 degrees C for 2 h gave a 98:2 mixture of (Z)-1-(2-nonenyl)piperidine and 1-(1-n-hexyl-2-propenyl)piperidine in 86% yield, No E isomer was obtained. Various (Z) allylic amines were obtained in 91-100% selectivity by allylic amination of methyl (Z) 3-monosubstituted-2-alkenyl carbonate.
• A novel reaction of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) to form 2-fluoro-2-trifluoromethyl-4-alkenamide
  作者：Ken-ichi Ogu、Motohiro Akazome、Katsuyuki Ogura

  DOI：10.1016/s0022-1139(03)00191-x

  日期：2003.11

  Treatment of allylic alcohols with hexafluoropropene-diethylamine adduct (PPDA) afforded N,N-diethyl-2-fluoro-2-trifluoromethyl-4-alkenamides which were formed by the Claisen rearrangement of intermediary 2-alkenyl-1-diethylamino-2,3,3,3-tetrafluoro-1-propenyl ethers. Although (E)-allylic alcohols gave two diastereomeric products in about 1:1 ratio, (Z)-allylic alcohols gave the corresponding product as a single diastereomer. (C) 2003 Elsevier B.V. All rights reserved.
• Palladium-catalyzed cross-coupling of aryl halides and olefinic epoxides via palladium migration
  作者：Richard C. Larock、Wai Yee Leung

  DOI：10.1021/jo00313a006

  日期：1990.12

  The palladium-catalyzed cross-coupling of aryl halides and olefinic epoxides bearing one to ten carbons between the two functional groups affords good yields of arylated allylic alcohols by a palladium migration process.