(1S,2R)-2-Chloro-1-phenyl-but-3-en-1-ol

• 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: (1S,2R)-2-Chloro-1-phenyl-but-3-en-1-ol
• 英文别名: (1S,2R)-2-chloro-1-phenylbut-3-en-1-ol
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: CDLBYJPVPZUSBR-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (1S,2R)-2-Chloro-1-phenyl-but-3-en-1-ol 在 indium(III) chloride 、 indium 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以76%的产率得到1-苯-1,3-丁二烯
  参考文献：
  名称：

  Indium-Mediated Reductive Elimination of Halohydrins

  摘要：

  Olefin formation has been successfully carried out by reductive elimination reactions of halohydrins with Pd(PPh3)(4)/In/InCl3 in aqueous media.

  DOI：

  10.1021/jo0262964
• 作为产物：
  描述：

  1-chloro-3-iodoprop-1(Z)-ene 、 苯甲醛 在 tin(ll) chloride 作用下， 生成 (1S,2R)-2-Chloro-1-phenyl-but-3-en-1-ol 、 (1S,2S)-2-chloro-1-phenylbut-3-en-1-ol
  参考文献：
  名称：

  简单，立体选择性，室温下合成顺式乙烯基环氧乙烷和反式1-苯基-1,3-丁二烯

  摘要：

  1-氯-3-碘丙-1-烯和SnCl 2在二甲基甲酰胺中的有机锡试剂通过氯取代的碳原子与醛反应。然后用NaOMe处理得到具有良好立体选择性的乙烯基环氧乙烷。在两当量的SnCl 2存在下，苯甲醛和1-溴-3-碘丙-1-烯仅产生-1-苯基-1,3-丁二烯。

  DOI：

  10.1016/s0040-4039(00)88249-0

文献信息

• Either γ-syn- or γ-anti-selective palladium-catalysed carbonyl allylation by mixed (E)- and (Z)-1,3-dichloropropene with tin(II) halides
  作者：Yoshiro Masuyama、Akihiro Ito、Yasuhiko Kurusu

  DOI：10.1039/a707865j

  日期：——

  Palladium-catalysed carbonyl allylations by mixed (E)- and (Z)-1,3-dichloropropene with SnI2–Bu4NI and SnCl2 diastereoselectively produce syn and anti 1-substituted 2-chlorobut-3-en-1-ols, respectively. These are transformed into cis and trans 1-substituted 2-vinyl epoxides.

  钯催化的醛丙烯化反应使用混合的（E）-和（Z）-1,3-二氯丙烯与SnI2-Bu4NI和SnCl2，分别以立体选择性方式生成syn和anti的1-取代的2-氯丁-3-烯-1-醇。这些产物进而转化为顺式和反式的1-取代的2-乙烯基环氧乙烷。
• Indium-mediated reaction of 1,3-dichloro- and 1,3-dibromopropenes with carbonyl compounds. Generation of novel 3,3-diindiopropene
  作者：Shuki Araki、Tsunehisa Hirashita、Hidetaka Shimizu、Hatsuo Yamamura、Masao Kawai、Yasuo Butsugan

  DOI：10.1016/0040-4039(96)01925-9

  日期：1996.11

  Indium-mediated reaction of 1,3-dichloropropene with aldehyde gave syn-chlorohydrin predominantly. A similar reaction of 1,3-dibromopropene gave viayloxirane and homoallyl alcohol; the former is formed from γ-bromoallylindium via the corresponding bromohydrin, and the latter is considered to be derived from a unique allylic diindium reagent, 3,3-diindiopropene.

  铟介导的1，3-二氯丙烯与醛的反应主要生成顺氯醇。1，3-二溴丙烯的类似反应得到硅烷基环氧乙烷和高烯丙基醇；前者是由γ-溴烯丙基经由相应的溴代醇形成的，后者被认为衍生自独特的烯丙基二铟试剂3,3-二茚二丙烯。
• Synthesis of Optically Active <i>syn</i>- and <i>anti</i>-Chlorohydrins through a Bienzymatic Reductive Cascade
  作者：Jorge González-Rodríguez、Jesús Albarrán-Velo、Raquel G. Soengas、Iván Lavandera、Vicente Gotor-Fernández、Humberto Rodríguez-Solla

  DOI：10.1021/acs.orglett.2c02592

  日期：2022.10.7

  1-aryl-2-chlorobut-2-en-1-ones. For the synthesis of these α-chloroenones, a two-step sequence was developed consisting of the allylation of the corresponding aldehyde with 3-dichloroprop-1-ene, followed by oxidation and further isomerization. The selective cooperative catalytic system involving ene-reductases (EREDs) and alcohol dehydrogenases (ADHs) afforded the desired optically active chlorohydrins under mild

  设计并优化了双酶级联反应，从相应的 1-aryl-2-chlorobut-2-en-1-ones 开始获得对映体纯的氯代醇。对于这些 α-氯烯酮的合成，开发了一个两步序列，包括相应醛与 3-二氯丙-1-烯的烯丙基化，然后氧化和进一步异构化。涉及烯还原酶 (ERED) 和醇脱氢酶 (ADH) 的选择性协同催化系统在温和的反应条件下以优异的转化率（高达 >99%）和选择性（高达 >99:1 的非对映异构比）提供了所需的光学活性氯醇（ dr), >99% 对映体过量 ( ee ))。
• Chiral Phosphoric Acid-Catalyzed Enantio- and Diastereoselective Allylboration of Aldehydes with β,γ-Substituted Allylboronates
  作者：Jinping Yuan、Pankaj Jain、Jon C. Antilla

  DOI：10.1021/acs.joc.2c00764

  日期：2022.6.17

  The catalytic asymmetric addition of β,γ-substituted allylboronates to aldehydes has been described. Promoted by 5 mol % chiral phosphoric acid, the reactions were broadly applicable, scalable, and efficient, allowing for the formation of 3,4-anti/syn-homoallylic alcohols bearing adjacent tertiary or quaternary stereogenic centers in a highly enantio- and diastereoselective manner (≤99% ee and dr >20:1)

  已经描述了 β,γ-取代的烯丙基硼酸酯对醛的催化不对称加成。在 5 mol% 手性磷酸的促进下，该反应具有广泛的适用性、可扩展性和高效性，允许以高度对映和非对映选择性的方式形成带有相邻叔或季立体中心的 3,4-反/同-高烯丙醇（≤99% ee 和 dr >20:1）。涉及手性磷酸的刚性椅子状过渡态有助于高度控制的反应。
• Diastereo- and Enantioselective Synthesis of <i>syn</i>-α-Vinylchlorohydrins and <i>cis</i>-Vinylepoxides
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1021/jo960875p

  日期：1996.1.1

  A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF3 . OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de greater than or equal to 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-alpha a-halohydrins (de greater than or equal to 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-gamma-chloroallyl]BIpc(2) leads to chiral syn-alpha-chlorohydrins and cis-vinylepoxides in high de (greater than or equal to 90%) and ee(90-99%). Enantioselectivity of reactions of chiral (Z)-(gamma-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other alpha-or gamma-substituted allylboranes. The effects of proportion ofBF(3) . OEt(2) and the relative efficacies of LiNR(2) bases on diastereo- and enantioselectivity of the chloroallylation are reported.