(S)-2-chloropentan-1-ol | 362044-83-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (S)-2-chloropentan-1-ol
• 英文别名: S-(-)-2-chloro-1-pentanol；(2S)-2-chloropentan-1-ol
• CAS: 362044-83-5
• 化学式: C₅H₁₁ClO
• 分子量: 122.595
• InChiKey: BSPZHSJUMXYBOD-YFKPBYRVSA-N

物化性质

• 沸点：
  162.5±13.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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)-2-chloropentan-1-ol 在 正丁基锂 、 sodium azide 、 palladium 10% on activated carbon 、 palladium on activated charcoal 、 氢气 、 三乙酰氧基硼氢化钠 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -70.0~135.0 ℃ 、344.75 kPa 条件下， 反应 83.58h， 生成 (R,S′)-5-(1-hydroxy-2-((1-(4-methoxyphenyl)pentan-2-yl)amino)ethyl)benzene-1,3-diol
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

  摘要：

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.030
• 作为产物：
  描述：

  L-正缬氨酸 在 盐酸 、 lithium aluminium tetrahydride 、 sodium nitrite 作用下， 以 乙醚 为溶剂， 反应 15.0h， 生成 (S)-2-chloropentan-1-ol
  参考文献：
  名称：

  琥珀木香：具有不同结构的酒精具有常见的嗅觉特征和对映异构体的明显差异

  摘要：

  只有一个的四个可能的反式的重要香料醇的异构体Norlimbanol ®（1）具有非常强的琥珀木质气味，异构体1A用（1' - [R，3小号，6'小号）绝对构型。它的对映异构体1B几乎无味，没有琥珀色木质特征，而非对映异构体1C和1D则较弱，只有最敏感的人才能察觉。同样是真实的全系列的感性类似物1，包括β-烷氧基醇。这些醚属于两个结构类别：[（2,2,6-三甲基环己基）氧基]-（参见3、4和16）或{[2-（叔丁基）环己基]氧基}烷-2-醇衍生物（见19和20 ;表）。允许各个羟基化侧链良好重叠的叠加模型为这两种类型的共有感知特性提供了初步的解释（图5）。亲脂性环己烷部分在该模型中仅表现出最小的重叠，表明相当大的分子可能具有相同的气味。（S）-配置β可通过对映酮的对映选择性还原，方便地大规模获得-烷氧基醇（方案9）。

  DOI：

  10.1002/hlca.200490237

文献信息

• Mechanistically Guided Design of an Efficient and Enantioselective Aminocatalytic α-Chlorination of Aldehydes
  作者：George Hutchinson、Carla Alamillo-Ferrer、Jordi Burés

  DOI：10.1021/jacs.1c02997

  日期：2021.5.12

  The enantioselective aminocatalytic α-chlorination of aldehydes is a challenging reaction because of its tendency to proceed through neutral intermediates in unselective pathways. Herein we report the rational shift to a highly selective reaction pathway involving charged intermediates using hexafluoroisopropanol as solvent. This change in mechanism has enabled us to match and improve upon the yields

  醛的对映选择性氨基催化 α-氯化是一个具有挑战性的反应，因为它倾向于在非选择性途径中通过中性中间体进行。在这里，我们报告了向高选择性反应途径的合理转变，该反应途径涉及使用六氟异丙醇作为溶剂的带电中间体。这种机制的变化使我们能够匹配和改进先前方法显示的产率和对映选择性，同时使用更便宜的氨基催化剂和氯化剂，催化剂用量减少 80-95%，温度方便，反应时间更短。
• A General Method for the Synthesis of Nonracemic <i>trans</i>-Epoxides:  Concise Syntheses of <i>trans</i>-Epoxide-Containing Insect Sex Pheromones
  作者：Baldip Kang、Robert Britton

  DOI：10.1021/ol702273n

  日期：2007.11.1

  developed that provides rapid access to alkyl-, alkenyl-, alkynyl-, and phenyl-substituted trans-epoxides from aldehydes. This methodology has also been applied in concise and high-yielding syntheses of both trans-epoxide containing insect sex pheromones.

  已经开发了用于合成手性非外消旋反式环氧化物的通用方法，该方法提供了从醛类快速进入烷基，烯基，炔基和苯基取代的反式环氧化物的途径。该方法也已用于含有反式环氧化物的昆虫性信息素的简明和高产合成中。
• Liquid crystalline mixtures having a chiral tilted smectic phase
  申请人：Hoffmann-La Roche Inc.

  公开号：US05242619A1

  公开（公告）日：1993-09-07

  Optically active compounds of the formula ##STR1## wherein rings A, B and C each independently are unsubstituted or each are 1,4-phenylene substituted with at least one of halogen-, cyano-, methyl- or methoxy in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; R.sup.1 is a radical of an optically active terpene alcohol after cleavage of the hydroxy group or a group --(CH.sub.2).sub.m --C*HX.sup.1 --R.sup.3 ; R.sup.2 is a radical of an optically active terpene alcohol after cleavage of the hydroxy group or a group --(CH.sub.2).sub.n --C*HX.sup.2 --R.sup.4 ; m and n each independently stand for the number O or 1: C* denotes a chiral carbon atom; X.sup.1 and X.sup.2 each independently are fluorine, chlorine, cyano, methyl or methoxy; R.sup.3 and R.sup.4 each independently denote a group R, phenyl or phenyl substituted with R, with the proviso that R.sup.3 is different from X.sup.1 and R.sup.4 is different from X.sup.2 ; R is an alkyl group in which optionally one methylene group is replaced by oxygen and/or optionally one group CH--CH is replaced by a group C.dbd.C; with the proviso that R.sup.1 and R.sup.2 are not simultaneously 2-alkyl when rings A, B and C together are p-terphenyl, as well as liquid crystalline mixtures and their use for electro-optical purposes.

  该公式的光学活性化合物如下：其中环A、B和C各自独立地未被取代，或者每个环是1,4-苯基取代物，至少有一个卤素、氰基、甲基或甲氧基，其中可以选择地1个CH基团或2个CH基团被氮取代；R^1是光学活性萜醇的基团，在羟基裂解后或者一个基团--(CH_2)_m--C*HX^1--R^3；R^2是光学活性萜醇的基团，在羟基裂解后或者一个基团--(CH_2)_n--C*HX^2--R^4；m和n各自独立地代表数字0或1：C*表示一个手性碳原子；X^1和X^2各自独立地是氟、氯、氰基、甲基或甲氧基；R^3和R^4各自独立地表示一个基团R、苯基或取代R的苯基，但R^3与X^1不同，R^4与X^2不同；R是一个烷基基团，其中可以选择地一个亚甲基基团被氧取代和/或可以选择地一个基团CH--CH被一个基团C.dbd.C取代；但R^1和R^2不同时为2-烷基，当环A、B和C共同为对联苯时，以及液晶混合物及其用于电光目的。
• Development of a Concise and General Enantioselective Approach to 2,5-Disubstituted-3-hydroxytetrahydrofurans
  作者：Baldip Kang、Jeffrey Mowat、Thomas Pinter、Robert Britton

  DOI：10.1021/ol802711s

  日期：2009.4.16

  Concise syntheses of 2,5-disubstituted-3-hydroxytetrahydrofurans have been developed that provide access to each configurational isomer of this scaffold from a single aldol adduct. Application of these methods to the rapid preparation of (6S,7S,9S,10S)- and (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol, two structurally related marine epoxylipids, is reported.

  已经开发了2，5-二取代的-3-羟基四氢呋喃的简明合成方法，其提供了从单个羟醛加合物获得该支架的每个构型异构体的途径。这些方法在快速制备（6 S，7 S，9 S，10 S）-和（6 S，7 S，9 R，10 R）-6,9-epoxynonadec-18-ene-7，中的应用据报道10-二醇是两种与结构相关的海洋环氧脂质。
• Optically active, oxygenated, alicyclic compounds and their use as perfuming ingredients
  申请人：FIRMENICH SA

  公开号：EP1136061B1

  公开（公告）日：2007-01-03