(Z)-hept-3-en-2-ol | 67077-40-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-hept-3-en-2-ol
• 英文别名: cis-Hepten-(3)-ol-(2)；hept-3c-en-2-ol
• CAS: 67077-40-1
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: BOEWENCXVIMZRU-WAYWQWQTSA-N

物化性质

• 沸点：
  159.4±8.0 °C(Predicted)
• 密度：
  0.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (Z)-hept-3-en-2-ol 在 palladium on activated charcoal mercury(II) diacetate 、 氢气 作用下， 生成 3-propylhexanal
  参考文献：
  名称：

  The Steric Course of the Claisen Rearrangement

  摘要：

  An infrared study of the stereochemistry attending the Claisen rearrangement of cis- and trans-alpha,gamma-dimethylallyl and two other related vinyl ethers has shown that the reaction produces essentially only trans substituted allylacetaidehydes. The double bond in the o-Claisen rearrangement product of trans-alpha, gamma-dimethylallyl phenyl ether has also been demonstrated by infrared absorption to be predominantly trans. The transition state geometry of the Claisen rearrangement implied by these findings is discussed.

  DOI：

  10.1021/ja01502a057
• 作为产物：
  描述：

  顺-2-己烯-1-醇 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (Z)-hept-3-en-2-ol
  参考文献：
  名称：

  钯催化的烯醇的对映体选择性氧化还原-中继Heck炔基化反应，以达到炔丙基立体中心。

  摘要：

  使用新的吡啶恶唑啉配体公开了二和三取代的烯醇的对映选择性的氧化还原-继电器Heck炔基化以构建炔丙基立体中心。与更传统的共轭加成方法相比，该策略允许使用烯丙醇底物直接获得手性β-炔基羰基化合物。

  DOI：

  10.1002/anie.201703089

文献信息

• Chloroperoxidase-catalyzed asymmetric oxidations: substrate specificity and mechanistic study.
  作者：Aleksey Zaks、David R. Dodds

  DOI：10.1021/ja00147a001

  日期：1995.10

  The substrate specificity of chloroperoxidase from Caldaromyces fumago in a number of halide-independent reactions was investigated and the ability of this enzyme to perform benzylic hydroxylations with high enantioselectivity is revealed. The substrate repertoire of chloroperoxidase is expanded and the enantioselectivity data for synthetically useful epoxidations are reported. The enzyme epoxidizes straight chain aliphatic and cyclic cis-olefins in a highly stereoselective manner favoring small unsubstituted substrates in which the double bond is not more than two carbon atoms from the terminal. The epoxidation of short-chain prochiral terminal dienes proceeds with high diastereoselectivity and moderate enantioselectivity, yielding monoepoxides exclusively. Unsubstituted straight-chain terminal olefins seven carbons or longer are epoxidized poorly. Aliphatic and aromatic alcohols are efficiently oxidized to aldehydes and acids. The utilization of radical probe substrate trans-2-phenyl-1-methylcyclopropane revealed that the mechanism of chloroperoxidase-catalyzed hydroxylation is incompatible with the existence of a discrete radical intermediate and most likely proceeds via transfer of the oxygen atom from the high valent iron oxo intermediate directly to the substrate.
• FRANKEL, E. N.;GARWOOD, R. F.;VINSON, J. R.;WEEDON, B. C. L., J. CHEM. SOC. PERKIN TRANS., 1982, N 11, 2715-2717
  作者：FRANKEL, E. N.、GARWOOD, R. F.、VINSON, J. R.、WEEDON, B. C. L.

  DOI：——

  日期：——
• The Steric Course of the Claisen Rearrangement
  作者：Albert W. Burgstahler

  DOI：10.1021/ja01502a057

  日期：1960.9

  An infrared study of the stereochemistry attending the Claisen rearrangement of cis- and trans-alpha,gamma-dimethylallyl and two other related vinyl ethers has shown that the reaction produces essentially only trans substituted allylacetaidehydes. The double bond in the o-Claisen rearrangement product of trans-alpha, gamma-dimethylallyl phenyl ether has also been demonstrated by infrared absorption to be predominantly trans. The transition state geometry of the Claisen rearrangement implied by these findings is discussed.
• Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols To Access Propargylic Stereocenters
  作者：Zhi-Min Chen、Christine S. Nervig、Ryan J. DeLuca、Matthew S. Sigman

  DOI：10.1002/anie.201703089

  日期：2017.6.1

  An enantioselective redox-relay Heck alkynylation of di- and trisubstituted alkenols to construct propargylic stereocenters is disclosed using a new pyridine oxazoline ligand. This strategy allows direct access to chiral β-alkynyl carbonyl compounds employing allylic alcohol substrates in contrast to more traditional conjugate addition methods.

  使用新的吡啶恶唑啉配体公开了二和三取代的烯醇的对映选择性的氧化还原-继电器Heck炔基化以构建炔丙基立体中心。与更传统的共轭加成方法相比，该策略允许使用烯丙醇底物直接获得手性β-炔基羰基化合物。