(3S,5Z)-1-phenyl-5-heptene-3-ol | 261917-84-4

• 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: (3S,5Z)-1-phenyl-5-heptene-3-ol
• 英文别名: (5Z,3S)-1-phenylhept-5-en-3-ol；(S,Z)-1-phenylhept-5-en-3-ol；(Z,3S)-1-phenylhept-5-en-3-ol
• CAS: 261917-84-4
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: FLYNSFDHIKHIAI-XQJDBVBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  溶剂黄146 、 肉桂醛 、 (3S,5Z)-1-phenyl-5-heptene-3-ol 在 三氟甲磺酸 作用下， 反应 20.0h， 以56.8%的产率得到(2R,3R,4R,6S)-4-acetoxy-3-methyl-2-(2-phenylethenyl)-6-(2-phenethyl)tetrahydropyran
  参考文献：
  名称：

  通过旋光性均烯丙基醇与醛的Prins环化反应（PCR）方便地合成高旋光性2,3,4,6-四取代的四氢吡喃

  摘要：

  旋光性均烯醇R a C * H（OH）CH 2 CHCHCH 3（1-取代的丁-2-烯-1-醇）与醛（R b CHO）的Prins环化反应（PCR）酸催化剂（HX）以良好的产率高度立体选择性地提供（2-R b，3-CH 3，4 -X，6-R a）-四取代的四氢吡喃。

  DOI：

  10.1016/j.tet.2005.12.054
• 作为产物：
  描述：

  苯丙醛 、 (1R,2R,5R)-1-(1'R-methylallyl)isomenthol 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以88%的产率得到(3S,5Z)-1-phenyl-5-heptene-3-ol
  参考文献：
  名称：

  通过由（+）-异薄荷酮制备的手性烯丙基供体的烯丙基转移反应，实现醛的新型对映选择性（2Z）-烷-2-烯基化。

  摘要：

  通过手性烯丙基供体的烯丙基转移反应成功实现了醛类的高对映选择性（2Z）-烷-2-烯基化反应，该反应很容易通过分离衍生自（ +）-异ment酮与烷-2-烯基氯化镁。[反应：看文字]

  DOI：

  10.1021/ol0400140

文献信息

• Highly Stereoselective Synthesis of<i>Z</i>-Homoallylic Alcohols by Kinetic Resolution of Racemic Secondary Allyl Boronates
  作者：Celia A. Incerti-Pradillos、Mikhail A. Kabeshov、Andrei V. Malkov

  DOI：10.1002/anie.201300709

  日期：2013.5.10

  α to Z: Racemic α‐chiral allyl boronates, which are readily synthesized from the respective primary allyl halides, undergo a highly efficient kinetic resolution in a face‐ and Z‐selective allylation of aldehydes catalyzed by the chiral Brønsted acid (R)‐TRIP (see scheme; Epin=tetraethylethylene glycol).

  α到 Z：外消旋的α-手性烯丙基硼酸酯，很容易从相应的伯烯丙基卤化物合成，在手性布朗斯台德酸（R）-TRIP催化的醛的Z面和Z选择性烯丙基化反应中经历高效的动力学拆分（参见方案； Epin ＝四乙基乙二醇）。
• New and Stereoselective Synthesis of 1,4-Disubstituted Buten-4-ols (Homoallylic Alcohol α-Adducts) from the Corresponding γ-Isomers (3,4-Disubstituted Buten-4-ols) via an Acid-Catalyzed Allyl-Transfer Reaction with Aldehydes
  作者：Shin-ichi Sumida、Masanori Ohga、Junji Mitani、Junzo Nokami

  DOI：10.1021/ja990057p

  日期：2000.2.1

  from aldehydes via the usual reaction with common allylic metals 1, were converted to the corresponding α-adducts 6 by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti- and syn-γ-adducts 3 gave E- and Z-α-adducts 6, respectively, and the optical purity of the γ-adducts 3 was transferred to the α-adducts 6 with >98%ee. This suggests that the allyl-transfer reaction proceeds

  高烯丙基醇 3 的 γ-加合物通过与常见烯丙基金属 1 的通常反应从醛衍生，通过酸催化的烯丙基转移反应转化为相应的 α-加合物 6。在烯丙基转移反应中，反-和顺-γ-加合物3分别得到E-和Z-α-加合物6，γ-加合物3的光学纯度转移到α-加合物6，>98 %ee。这表明烯丙基转移反应通过六元环状过渡态 [T] 立体选择性地进行。该反应由各种金属三氟甲磺酸盐以及路易斯酸和布朗斯台德酸催化。
• Highly (<i>E</i>)-Selective BF₃·Et₂O-Promoted Allylboration of Chiral Nonracemic α-Substituted Allylboronates and Analysis of the Origin of Stereocontrol
  作者：Ming Chen、William R. Roush

  DOI：10.1021/ol1007444

  日期：2010.6.18

  delta-Methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z>30:1 and 93% to >95% ee via BF3 center dot Et2O-promoted allylboration with alpha-Me-allylboronate 1. The origin of high (E)-selectivity is proposed.
• An Unusual Approach to the Synthesis of Enantiomerically Cis Linear Homoallylic Alcohols Based on the Steric Interaction Mechanism of Camphor Scaffold
  作者：Chi-Lik Ken Lee、Cheng-Hsia Angeline Lee、Kui-Thong Tan、Teck-Peng Loh

  DOI：10.1021/ol049633z

  日期：2004.4.1

  Camphor is used as the chiral auxiliary for the enantioselective synthesis of cis linear homoallylic alcohols. A range of catalysts, aldehydes, and solvents were investigated to obtain the optimum yield, enantioselectivity, and cis olefinic geometry.
• A Novel Enantioselective (2<i>Z</i>)-Alk-2-enylation of Aldehydes via an Allyl-Transfer Reaction from Chiral Allyl Donors Prepared from (+)-Isomenthone
  作者：Junzo Nokami、Kenta Nomiyama、Siddiqi M. Shafi、Kazuhide Kataoka

  DOI：10.1021/ol0400140

  日期：2004.4.1

  A highly enantioselective (2Z)-alk-2-enylation of aldehydes was successfully achieved by an allyl-transfer reaction from a chiral allyl donor, which was easily obtained by separation of a diastereomeric mixture of the corresponding homoallylic alcohol gamma-adducts derived from (+)-isomenthone with alk-2-enylmagnesium chloride. [reaction: see text]

  通过手性烯丙基供体的烯丙基转移反应成功实现了醛类的高对映选择性（2Z）-烷-2-烯基化反应，该反应很容易通过分离衍生自（ +）-异ment酮与烷-2-烯基氯化镁。[反应：看文字]