(S)-1-(2-溴苯基)丙烷-1-醇 | 170379-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-(2-溴苯基)丙烷-1-醇
• 英文名称: (1S)-1-(2-bromophenyl)propan-1-ol
• 英文别名: (S)-o-(1-hydroxy-1-propyl)bromobenzene；(S)-1-(2'-bromophenyl)propan-1-ol；(S)-1-(2-bromophenyl)-1-propanol；(S)-1-(2-bromophenyl)propan-1-ol；(S)-1-(o-bromophenyl)-1-propanol；(S)-1-(2-bromophenyl)propanol
• CAS: 170379-92-7
• 化学式: C₉H₁₁BrO
• 分子量: 215.09
• InChiKey: SMYHFDLFOKKDOO-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (S)-1-(2-溴苯基)丙烷-1-醇 在 selenium 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (S,S)-bis[2-(1-hydroxypropyl)phenyl] diselenide
  参考文献：
  名称：

  Wirth, Thomas, Angewandte Chemie, 1995, vol. 107, # 16, p. 1872 - 1873

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-溴苯基)丙烷-1-酮 在 Rhizopus arrhizus 作用下， 以 乙醇 为溶剂， 反应 192.0h， 以58%的产率得到(S)-1-(2-溴苯基)丙烷-1-醇
  参考文献：
  名称：

  Asymmetric reduction of halo-substituted arylalkanones with Rhizopus arrhizus

  摘要：

  The Rhizopus arrhizus-mediated asymmetric reduction of various haloaryl alkanones furnished the respective (S)-carbinols with good to excellent enantioselectivities. it was found that the reaction course was primarily governed by the relative position of the halogen with respect to the carbonyl group. and its size. The relative order of efficacies of the nature of the halogen and their substitution pattern were Br > Cl > F and o- > p- > m-. The ortho-effect was the most predominant factor in the stereochemical outcome of the reaction, which was also confirmed with some non-halo-substituted acetophenones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.035

文献信息

• New and Efficient Chiral Selenium Electrophiles
  作者：Lars Uehlin、Gianfranco Fragale、Thomas Wirth

  DOI：10.1002/1521-3765(20020301)8:5<1125::aid-chem1125>3.0.co;2-i

  日期：2002.3.1

  New chiral diselenides were prepared in a few steps from readily available starting materials. The selenium electrophiles generated from these diselenides were used for the efficient stereoselective inter- and intramolecular functionalization of alkenes. The substitution pattern influences the stereoselectivities and protection of the hydroxy moiety in the chiral side chain led to increased selectivities

  从现有的起始原料中分几步制备新的手性二硒化物。从这些二硒化物生成的硒亲电子试剂用于烯烃的高效立体选择性分子间和分子内官能化。取代模式影响手性侧链中的立体选择性和羟基部分的保护，从而导致硒基化反应中选择性和产率的提高。在第二邻位的另外的取代基也是有利的。获得具有高达96％de的加成产物。在一定程度上也研究了亲核试剂对烯烃亚硒化反应的影响。
• First Detection of a Selenenyl Fluoride ArSe?F by NMR Spectroscopy: The Nature of Ar2Se2/XeF2 and ArSe?SiMe3/XeF2 Reagents
  作者：Helmut Poleschner、Konrad Seppelt

  DOI：10.1002/chem.200400596

  日期：2004.12.17

  Arylselenenyl fluorides ArSeF are obtained from diselenides Ar2Se2 or arylselenotrimethylsilanes ArSe-SiMe3, and XeF2. They are detected by low-temperature 19F and 77Se NMR spectroscopy. Substitution in the ortho position of the aromatic ring to provide electronic or steric protection is a requirement for their formation. ArSe--F compounds decompose according to 3 ArSe-F-->[ArSe-SeF2Ar]+ArSe-F-->ArSeF3+Ar2Se2

  从二硒化物Ar 2 Se 2或芳基硒代三甲基硅烷ArSe-SiMe 3和XeF 2获得芳基硒烯基氟化物ArSeF。通过低温19F和77Se NMR光谱检测到它们。芳香环的邻位取代以提供电子或空间保护是其形成的要求。ArSe-F化合物根据3 ArSe-F-> [ArSe-SeF2Ar] + ArSe-F-> ArSeF3 + Ar2Se2分解。已经使用MP2，CCSD（T）和B3 LYP方法计算了这种歧化反应的反应能以及硫和碲同系物的反应能。发现它们在序列S中放热越来越大
• Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols
  作者：Masatoshi Asami、Naomichi Miyairi、Yukihiro Sasahara、Ken-ichi Ichikawa、Naoya Hosoda、Suguru Ito

  DOI：10.1016/j.tet.2015.07.031

  日期：2015.9

  alcohols, synthesized from (R)-1-phenylethylamine, were used as chiral ligands for the enantioselective addition of diethylzinc to benzaldehyde. (S)-1-Phenyl-1-propanol was obtained with high enantioselectivity in all cases since the stereochemical outcome of the reaction was controlled by the chiral benzylic carbon bearing amino group. Highest catalytic activity was obtained by using (R)-1-2-[1-(pyrroli

  由（R）-1-苯基乙胺合成的一系列邻亚二甲苯基型1，4-氨基醇被用作手性配体，用于将二乙基锌对映选择性地加成到苯甲醛中。在所有情况下，由于反应的立体化学结果是由带有手性苄基碳原子的氨基控制的，因此在所有情况下都以高对映选择性获得了（S）-1-苯基-1-丙醇。通过使用衍生自（R）-1-（1-苯乙基）的（R）-1- 2- [1- [吡咯烷-1-基）乙基]苯基}环己-1-醇（1n）获得最高的催化活性。吡咯烷和环己酮。在1n的存在下，二乙基锌与醛的反应可制得各种手性仲醇。 在2小时内具有良好的对映选择性。
• C2-Symmetric N-(.BETA.-Mercaptoethyl)pyrrolidine as a Chiral Catalyst Ligand in the Addition Reaction of Aldehydes and Diethylzinc.
  作者：Yukio MASAKI、Yukihiro SATOH、Takechi MAKIHARA、Min SHI

  DOI：10.1248/cpb.44.454

  日期：——

  A chiral C2-symmetric N-(β-mercaptoethyl)pyrrolidine bearing 6-membered benzylidene acetal functionalities fused at the 2, 3- and 4, 5-positions was found to exhibit high efficiency in the asymmetric addition reaction of aldehydes with diethylzinc.

  一种具有C2对称性的手性N-(β-巯基乙基)吡咯烷，其在2、3位和4、5位融合了6元环苄亚胺醚官能团，被发现对醛与二乙基锌的不对称加成反应表现出高效性。
• Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by titanium-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol complex
  作者：Fu-Yao Zhang、Albert S.C. Chan

  DOI：10.1016/s0957-4166(97)00501-6

  日期：1997.11

  The use of Ti(H8-BINOL) (H8-BINOL=5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol) as a catalyst for the diethylzinc addition to aldehydes has been studied, and high e.e.s (up to 98.5%) were obtained for the chiral alcohol products. The results were significantly better than those obtained with the corresponding Ti(BINOL) catalyst (BINOL=1,1′-bi-2-naphthol).

  Ti（H 8 -BINOL）（H 8 -BINOL = 5,5'，6,6'，7,7'，8,8'-八氢-1,1'-bi-2-萘酚）的用途已经研究了用于将二乙基锌加成醛的催化剂，并且对于手性醇产物获得了高ee（高达98.5％）。结果明显好于用相应的Ti（BINOL）催化剂（BINOL = 1,1'-bi-2-萘酚）获得的结果。