[1,1-(2)H2]-2-氯乙醇 | 77081-40-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 中文名称: [1,1-(2)H2]-2-氯乙醇
• 英文名称: <1,1-(2)H2>-2-Chloroethanol
• 英文别名: 2-chloro<1,1-2H2>ethanol；2-chloro-1,1-dideuterioethanol；2-chloro-1,1-dideuteroethanol；2-Chloroethanol-1,1-d2
• CAS: 77081-40-4
• 化学式: C₂H₅ClO
• 分子量: 82.4982
• InChiKey: SZIFAVKTNFCBPC-CBTSVUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  4
• 可旋转键数：
  1
• 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：

  [1,1-(2)H2]-2-氯乙醇 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  水性铂络合物活化CH的机理研究

  摘要：

  据报道，通过拟议的（烷基）Pt II和（烷基）Pt IV中间体，[PtCl 6 ] 2- / [PtCl 4 ] 2-水溶液将烷烃氧化为醇和烷基氯化物的详细机理研究。[PtCl 4 ] 2−与RI（R = CH 3，CH 2 CH 2 OH）在水中的反应生成[PtCl 5 R] 2−，将其分离为NMe 4盐。其分解的动力学速率定律在氯化物水溶液以ROH和RCl的支持小号Ñ由Cl 2的位移-或H 2 O作为最后一步的机理。赤和苏式- [氯铂酸5（CHDCHDOH）] 2-通过氧化得到[氯铂酸3（反式-和顺-CHDCHD）] -分别与有Cl反应-与碳的立体化学的反转，与一致的该小号ñ 2机构。[PtCl 5（CH 2 CH 2 OH）] 2-也是通过用[PtCl 6 ] 2-氧化蔡司盐而获得的。。动力学表明水对协调乙烯即攻击得到的Pt的β羟基乙基先于氧化II与Pt IV，而不是相反的顺序，并

  DOI：

  10.1016/0022-328x(95)05567-9
• 作为产物：
  描述：

  氯乙酸甲酯 在 lithium aluminium deuteride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以49%的产率得到[1,1-(2)H2]-2-氯乙醇
  参考文献：
  名称：

  Synthesis, isolation, and reactivity of a deuterated mustard simulant: 2-(phenylthio)ethyl-2,2-d2 chloride

  摘要：

  We have achieved the synthesis and isolation, without substantial label scrambling, of 2-(phenylthio)-ethyl-2,2-d2 chloride (2-Cl), a compound useful in modeling reactions of mustard and other highly reactive beta-thioethyl chlorides. 2-Cl undergoes slow label scrambling upon dissolution in hot, dry acetonitrile or acetone. Rates of scrambling of the deuterium label in 2-Cl have been measured by following proton NMR changes. Our present work clearly demonstrates that cyclic sulfonium ions are involved in these scrambling reactions. In anhydrous or aqueous acetone, thiourea traps the sulfonium ion intermediate to give stable, label-scrambled thiouronium salts. In anhydrous acetone, in competition with formation of the thiouronium salts, chloride return occurs giving 2-Cl and its label-scrambled isomer, 2-(phenylthio)ethyl-1,1-d2 Chloride (1-Cl). However, no chloride return is observed in 60% aqueous acetone. Mechanistic implications of these results are presented.

  DOI：

  10.1021/jo00075a050

文献信息

• Synthesis of specifically deuterium labeled sulfur and oxygen ether side-chain-extended antileukemic (2-chloroethyl)nitrosoureas and study of their products and pathways of decomposition under physiological conditions
  作者：J. William Lown、R. Rao Koganty、Alummoottil V. Joshua

  DOI：10.1021/jo00132a010

  日期：1982.5
• Synthesis and reactions of deuterated 2-(alkylimino)-3-nitrosooxazolidines, 3-alkyl-1-(2-hydroxyethyl)-1-nitrosoureas, and related compounds as possible intermediates in the aqueous decomposition of 3-alkyl-1-(2-chloroethyl)-1-nitrosoureas
  作者：J. William Lown、Shive M. S. Chauhan

  DOI：10.1021/jo00325a011

  日期：1981.6
• Formation of isomeric ethylenehalonium and α-haloethyl cations and the role of ion-neutral complexes in the decomposition of protonated β-haloethanols
  作者：Albert J. R. Heck、Leo J. de Koning、Nico M. M. Nibbering

  DOI：10.1002/oms.1210280317

  日期：1993.3

  AbstractDecomposition of protonated β‐haloethanols was found to proceed predominantly via the loss of water. The mechanism was studied in the decomposition of metastable and collisionally activated isotopically labelled protonated β‐haloethanols. The study involved the characterization of the resulting fragment ions by collisionally activated decomposition and by low‐pressure ion/molecule probe reactions. The results indicate that loss of water from protonated β‐haloethanols proceeds via two competing mechanisms. The competition between these mechanisms appears to be governed by the nature of the halogen and by the internal energy of the decomposing protonated β‐haloethanol. In the first mechanism, loss of water is considered to be initiated by a concerted 1,2‐elimination of H3O+ resulting in an ion–molecule complex between H3O+ and haloethene. Rapid and reversible proton transfers between the two species in the complex is followed by a relatively slow dissociation ofthe intermediate complex resulting in the formation of an water molecule and an α‐haloethyl cation. In competition with this mechanism, loss of water can be initiated by carbon–oxygen bond cleavage, which is assisted by halogen–carbon bond formation resulting in the formation of a water molecule and cyclic ethylenehalonium ion.
• Synthesis of (R)- and (S)-1-amino[2,2-2H2]cyclopropane-1-carboxylic acids
  作者：Pullachipatti K. Subramanian、Ronald W. Woodard

  DOI：10.1021/jo00377a003

  日期：1987.1
• McManus Samuel P., Karaman Rashid M., Sedaghat-Herati Reza, Hovanes Bruce+, J. Org. Chem, 58 (1993) N 23, S 6466-6469
  作者：McManus Samuel P., Karaman Rashid M., Sedaghat-Herati Reza, Hovanes Bruce+

  DOI：——

  日期：——