(R)-1-(3-fluorophenyl)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: (R)-1-(3-fluorophenyl)but-3-en-1-ol
• 英文别名: (1R)-1-(3-fluorophenyl)but-3-en-1-ol
• 化学式: C₁₀H₁₁FO
• 分子量: 166.195
• InChiKey: AFBZZQDKVXSARI-SNVBAGLBSA-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：
  2

反应信息

• 作为产物：
  描述：

  (+)-Ipc2B(烯丙基)硼烷 、 3-氟苯甲醛 在 sodium hydroxide 、 双氧水 作用下， 以 乙醚 、 正戊烷 、 甲醇 为溶剂， 反应 7.0h， 生成 (R)-1-(3-fluorophenyl)but-3-en-1-ol 、 (S)-1-(3-fluorophenyl)but-3-en-1-ol
  参考文献：
  名称：

  Highly enantioselective synthesis of (+)- and (−)-perfluoroalkyl(aryl) homoallyl alcohols

  摘要：

  Asymmetric allylboration of perfluoroaldehydes and fluorine substituted aromatic aldehydes with (d)Ipc(2)BAll and 2-Icr(2)BAll has been investigated. Both enantiomers of the fluorinated homoallyl alcohols were obtained in high yields and excellent enantiopurity (95-99% eel. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00456-0

文献信息

• Chiral Bisdiphenylphosphine Dioxides Bearing a Bis(triazolyl) Backbone as Promising Lewis Bases for Asymmetric Organocatalysis
  作者：Nicolas Sevrain、Jean-Noel Volle、Jean-Luc Pirat、Tahar Ayad、David Virieux

  DOI：10.1002/ejoc.201800317

  日期：2018.5.24

  Two new chiral diphenylphosphine dioxides bearing an original bis(triazolyl) backbone were prepared through a two‐step sequence. The key reaction involves a copper‐catalyzed [3+2] cycloaddition/dimerization reaction leading to the formation of five bonds in one chemical step with 100 % atom efficiency. Interestingly, these ligands exhibited good to excellent catalytic activities as chiral Lewis base

  通过两个步骤制备了两个带有原始双（三唑基）骨架的新手性二苯基二氧化膦。关键反应涉及铜催化的[3 + 2]环加成/二聚反应，导致在一个化学步骤中以100％的原子效率形成五个键。有趣地，这些配体表现出良好至优异的催化活性，因为手性路易斯碱有机催化剂促进有用的立体选择反应。
• Synthesis of axially chiral C10-BridgePHOS oxides and their use as organocatalysts in enantioselective allylations of aldehydes
  作者：Jianzhong Chen、Delong Liu、Dongyang Fan、Yangang Liu、Wanbin Zhang

  DOI：10.1016/j.tet.2013.07.030

  日期：2013.9

  of C10-BridgePHOS oxides possessing different substituted groups on the diphenyl phosphine system were synthesized and tested as organocatalysts in the allylation of aldehydes with allyltrichlorosilane, providing chiral homoallylic alcohols. These types of organocatalysts showed high catalytic activity and only 2 mol% catalyst loading was required to induce short reaction times. Under optimal reaction

  合成了一系列在二苯膦系统上具有不同取代基的C 10 -BridgePHOS氧化物，并作为醛与烯丙基三氯硅烷的烯丙基化反应的有机催化剂进行了测试，提供了手性均烯丙基醇。这些类型的有机催化剂显示出高催化活性，并且仅需要2 mol％的催化剂负载量即可缩短反应时间。在最佳反应条件下，对于多种底物，均获得了优异的产品收率和高达92％的ee。
• Axially chiral <i>N,N′‐</i> dioxides ethers for catalysis in enantioselective allylation of aldehydes
  作者：Shijie Wu、Yongfei Xing、Jie Wang、Xingchen Guo、Huajie Zhu、Wan Li

  DOI：10.1002/chir.23122

  日期：2019.11

  A series of axially chiral ethers synthesized from biscarboline N,N′‐dioxides, (S)‐1a to (S)‐1n, was investigated in enantioselectivity addition reactions of allyltrichlorosilane with a series of substituted aldehydes, including bulky substituted aldehydes. High enantioselectivities (up to 96%ee) were achieved using the catalyst (S)‐1k at 1 mol % loading.

  从biscarboline合成了一系列轴向手性醚Ñ，Ñ '-dioxides，（小号） - 1A至（小号） - 1N，在烯丙基三氯硅烷的对映选择性加成反应进行了研究了一系列取代的醛的，包括膨松取代的醛。使用负载量为1 mol％的催化剂（S）-1k可实现高对映选择性（高达96％ee）。
• A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes
  作者：Sharad V. Kumbhar、Chinpiao Chen

  DOI：10.1016/j.catcom.2020.106166

  日期：2021.1

  Asymmetric allylation and vinylation of aldehydes with allyl halides and vinyl halides have been achieved using the chromium(II)-oxazoline catalyst. The catalyst promotes the highly efficient enantioselective Nozaki–Hiyama-Kishi (NHK) allylation of aldehydes using allyl bromide, producing the corresponding homoallylic alcohols in good yields (up to 84%) and a high level of enantioselectivity (up to

  使用铬（II）-恶唑啉催化剂已经实现了醛与烯丙基卤和乙烯基卤的不对称烯丙基化和乙烯基化。该催化剂使用烯丙基溴促进醛的高效对映选择性Nozaki-Hiyama-Kishi（NHK）烯丙基化，以高产率（最高84％）和高对映选择性（最高98％ee）产生相应的均烯丙基醇。同时，醛的NHK乙烯基化可以以令人满意的产率（高达88％）和高水平的对映选择性（高达97％ee）生产出所需的烯丙醇。我们开发了一种可靠且温和的方案来制备手性均烯丙基和烯丙基醇。
• Addition of aldehydes with allyltrichlorosilane catalyzed by chiral bis-N–O secondary amides
  作者：Yu Deng、Wei Pan、Yu-Ning Pei、Jin-Liang Li、Bing Bai、Hua-Jie Zhu

  DOI：10.1016/j.tet.2013.09.088

  日期：2013.12

  l-tryptophan were prepared and used as organocatalysts in enantioselective allylation of aromatic aldehydes with allyltrichlorosilanes. The corresponding addition adducts homoallylic chiral alcohols obtained high enantioselectivities (up to 96% ee) when 1 mol % of catalyst was used. The unexpected result is the addition product's absolute configuration is R when (R)-chiral amides was used, in contrast, it was

  制备了从1-色氨酸衍生的新的轴向N-氧化物酰胺，并将其用作有机催化剂用于芳族醛与烯丙基三氯硅烷的对映选择性烯丙基化。当使用1mol％的催化剂时，相应的加成加合物均聚物手性醇获得高对映体选择性（至多96％ee）。出乎意料的结果是，当使用（R）-手性酰胺时，加成产物的绝对构型为R，相反，当将（R）-手性甲酯用于烯丙基化时，其加成产物的绝对构型为（S）。结果表明酰胺的N原子参与了过渡态过程。