(1R,2S)-2-chloro-1,2-diphenylethanol | 121652-14-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,2S)-2-chloro-1,2-diphenylethanol
• 英文别名: erythro-2-Chlor-1,2-diphenyl-aethanol
• CAS: 121652-14-0
• 化学式: C₁₄H₁₃ClO
• 分子量: 232.71
• InChiKey: ZCOFOBIIOQWUDE-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (1R,2S)-2-chloro-1,2-diphenylethanol 生成 Stilbene oxide
  参考文献：
  名称：

  KONOPELSKI, JOSEPH P.;BOEHLER, MARK A.;TARASOW, THEODORE M., J. ORG. CHEM., 54,(1989) N0, C. 4966-4970

  摘要：

  DOI：
• 作为产物：
  描述：

  erythro-1-Chlor-2-(formyloxy)-1,2-diphenylethan 在 titanium(IV) isopropylate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以85%的产率得到(1R,2S)-2-chloro-1,2-diphenylethanol
  参考文献：
  名称：

  Preparation of (1R,2S)- and (1S,2R)-2-chloro-1,2-diphenylethanol and other .beta.-halohydrins in enantiomerically pure form

  摘要：

  DOI：

  10.1021/jo00281a049

文献信息

• Enantiomerically pure vinylketene acetals in the Diels-Alder reaction. Catalysis and facial selectivity.
  作者：Mark A. Bochler、Joseph P. Konopelski

  DOI：10.1016/s0040-4020(01)86459-0

  日期：1991.1

  diastereoselective dienes in the Diels-Alder reaction have been developed. Most selective are (4R, 5R)-4,5-diphenyl-2-(2-methyl-2-propenidene)-1,3-dioxolane (8) and (4R, 5R)-4,5-diphenyl-2-((E)-2-butenidene)-1,3-dioxolane (9), which utilize phenyl rings as asymmetric directing groups. It was shown through NOE analysis that the major product obtained from the reaction of diene 9 and N-methylmaleimide

  已经开发了一系列对映体纯的乙烯基乙烯酮缩醛，其在Diels-Alder反应中起非对映选择性二烯的作用。选择性最高的是（4 R，5 R）-4,5-二苯基-2-（2-甲基-2-亚丙烯基）-1,3-二氧戊环（8）和（4 R，5 R）-4,5-二苯基-2-（（E）-2-丁烯）-1,3-二氧戊环（9），其利用苯环作为不对称的导向基团。通过NOE分析表明，由二烯9和N-甲基马来酰亚胺反应获得的主要产物是由于亲二烯体向二烯的Re exo途径，其中两个内过渡态也以少量出现在产物混合物中。确定过渡态能量的相对顺序为Re exo < Re endo < Si endo < Si exo。分子力学和π电荷密度计算均用于合理化在二烯8与N-甲基马来酰亚胺（48：1）反应中观察到的高非对映选择性。
• Enantioselective epoxide ring opening catalyzed by bis(tetrahydroisoquinoline) N,N′-dioxides
  作者：Aneta Kadlčíková、Klára Vlašaná、Martin Kotora

  DOI：10.1135/cccc2011024

  日期：——

  Four bis(tetrahydroisoquinoline) N,N′-dioxides were used as catalysts for the epoxide ring opening with tetrachlorosilane under various conditions. A strong solvent effect on asymmetric induction was observed for each of the used catalysts. The highest achieved asymmetric induction for the opening of meso-stilbene oxide was 69% ee. Regarding the cycloalkene oxides, 56% ee was obtained in the reaction with cyclooctene oxide.

  四种双(四氢异喹啉)N,N′-二氧化物被用作催化剂，用于在不同条件下与四氯硅烷开环环氧化物。观察到溶剂对对称诱导的影响。对于开环meso-苯乙烯环氧化物，最高达到的对称诱导率为69% ee。对于环烯氧化物，反应与环辛烯氧化物得到了56% ee。
• Acylketene acetals in organic synthesis.
  作者：Clark N. Eid、Joseph P. Konopelski

  DOI：10.1016/s0040-4020(01)80937-6

  日期：1991.1

  reactivity of achiral and enantiomerically pure acylketene acetals are described. The key reactions of these substrates involve facile conjugate hydroboration and organolithium addition. Enantiomerically pure acylketene acetals were employed to generate a homochiral β-keto ketal through a highly diastereoselective lithium enolate quench. This β-keto ketal, which was also prepared through a desymmetrization

  描述了非手性和对映体纯的酰基乙烯酮缩醛的制备和反应性。这些底物的关键反应涉及容易的共轭硼氢化和有机锂的添加。采用对映体纯的酰基乙烯酮缩醛，通过高度非对映选择性的烯醇锂猝灭反应生成同手性的β-酮缩酮。该β-酮缩酮，也通过对内消旋二酮的不对称缩酮化反应制得，被用于昆虫信息素sitophilure的合成。
• Enantiomerically pure ketals in synthesis. Diastereoselective formation of β-keto and β-hydroxy ketals
  作者：Clark N. Eid、Joseph P. Konopelski

  DOI：10.1016/s0040-4039(00)79468-8

  日期：1991.1

  Enantiomerically pure acylketene acetals were employed to generate a homochiral β-keto ketal through a highly diastereoselective lithium enolate quench. The β-keto ketal, which was also prepared through a desymmetrization ketalization reaction on a meso dione, was employed in the synthesis of the isomers of the insect pheromone sitophilure.

  采用对映体纯的酰基乙烯酮缩醛，通过高度非对映选择性的烯醇锂猝灭反应生成同手性的β-酮缩酮。β-酮缩酮，也通过对内消旋二酮的不对称缩酮化反应制得，被用于昆虫信息素固溶体的异构体的合成。
• Nucleophilic Reactions between Cyclic 1,2-Sulfites and Chloride Ions.
  作者：Kirsten Nymann、Linda Jensen、John S. Svendsen、T. Anthonsen、Ryszard Gawinecki、Günter Häfelinger、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0832

  日期：——

  When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohydrins are formed with low regio and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochemical outcome of the reactions. The results showed that reversible inversion pathways (S(N)2 reactions) and a retention pathway (S(N)2i reaction) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites.