carbonic acid tert-butyl ester 2-phenylethyl ester | 95932-33-5

• 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: carbonic acid tert-butyl ester 2-phenylethyl ester
• 英文别名: carbonic acid tert-butyl ester phenetyl ester；(2-phenylethyl) tert-butyl carbonate；tert-butyl phenethyl carbonate；Tert-butyl 2-phenylethyl carbonate
• CAS: 95932-33-5
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: HIGODUCJNINXMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  carbonic acid tert-butyl ester 2-phenylethyl ester 在 molybdenum(VI) oxychloride 、 氘代甲醇 作用下， 反应 290.0h， 以96%的产率得到phenyl ethanol-d1
  参考文献：
  名称：

  Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride

  摘要：

  Among five different oxidometallic species and two Lewis acids investigated, MoO(2)Cl(2) shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.024
• 作为产物：
  描述：

  苯乙醇 、 二碳酸二叔丁酯 在 MgO-ZrO₂ nanoparticle 作用下， 反应 2.0h， 以93%的产率得到carbonic acid tert-butyl ester 2-phenylethyl ester
  参考文献：
  名称：

  混合金属MgO–ZrO2纳米粒子在无溶剂条件下对醇和酚的O-叔-Boc保护

  摘要：

  描述了一种在无溶剂条件下由MgO-ZrO 2纳米粒子催化的醇和苯酚的O- ter - Boc保护的环境友好方法。各种苯酚，醇（脂肪族和芳香族）以良好或优异的收率（50-95％）转化为相应的O-tert- Boc产品。本方案在无溶剂条件下是方便，简单和有效的。MgO-ZrO 2 Nps可以很容易地由廉价的前体制备，并且可重复使用，可回收利用和化学选择性。版权所有©2012 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.2846

文献信息

• Heterobimetallic Dinuclear Lanthanide Alkoxide Complexes as Acid–Base Difunctional Catalysts for Transesterification
  作者：Ruijie Zeng、Hongting Sheng、Yongcang Zhang、Yan Feng、Zhi Chen、Junfeng Wang、Man Chen、Manzhou Zhu、Qingxiang Guo

  DOI：10.1021/jo5016536

  日期：2014.10.3

  practical lanthanide(III)-catalyzed transesterification of carboxylic esters, weakly reactive carbonates, and much less-reactive ethyl silicate with primary and secondary alcohols was developed. Heterobimetallic dinuclear lanthanide alkoxide complexes [Ln2Na8(OCH2CH2NMe2)}12(OH)2] (Ln = Nd (I), Sm (II), and Yb (III)) were used as highly active catalysts for this reaction. The mild reaction conditions enabled

  开发了一种实用的镧系元素（III）催化的羧酸酯，弱反应性碳酸酯和低反应性硅酸乙酯与伯醇和仲醇的酯交换反应。异双金属双核镧系醇盐配合物[Ln 2 Na 8 （OCH 2 CH 2 NMe 2）} 12（OH）2 ]（Ln = Nd（I），Sm（II）和Yb（III））用作该反应的高活性催化剂。温和的反应条件使各种底物的酯交换反应能够以良好或高收率进行。上述配合物可以作为协同作用的酸碱双官能催化剂，从而使酯交换反应得到有效活化，与简单的酸/碱催化剂相比，该络合物被认为具有更高的反应活性。
• The First Simple Method of Protection of Hydroxy Compounds as their <i>O</i>-Boc Derivatives under Lewis Acid Catalysis
  作者：Giuseppe Bartoli、Marcella Bosco、Armando Carlone、Renato Dalpozzo、Manuela Locatelli、Paolo Melchiorre、Paolo Palazzi、Letizia Sambri

  DOI：10.1055/s-2006-949609

  日期：2006.8

  The first Lewis acid catalyzed protection of alcohols as Boc derivatives is described. Zinc acetate is a very efficient catalyst for this transformation and the reaction can be applied to primary, secondary and aromatic alcohols, providing the first example of a generally applicable method.

  描述了第一个路易斯酸催化的醇作为 Boc 衍生物的保护。醋酸锌是这种转化的非常有效的催化剂，该反应可应用于伯醇、仲醇和芳香醇，提供了普遍适用方法的第一个例子。
• Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Vijay D. Pawar、Yogesh S. Munot、Shieu-Shien Weng、Cheng-Hsiu Ku、Cheng-Yuan Liu

  DOI：10.1021/jo048363v

  日期：2005.2.1

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.
• Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate
  作者：Chien-Tien Chen、Jen-Huang Kuo、Chun-Hsin Li、N. B. Barhate、Sang-Wen Hon、Tai-Wei Li、Shi-Deh Chao、Chia-Cheng Liu、Ying-Chieh Li、I-Hsin Chang、Jin-Sheng Lin、Chin-Jing Liu、Y-Chen Chou

  DOI：10.1021/ol016684c

  日期：2001.11.1

  [GRAPHICS]Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal triflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.
• Houlihan, F.; Bouchard, J.; Frechet, J. M. J., Canadian Journal of Chemistry, 1985, vol. 63, p. 153 - 162
  作者：Houlihan, F.、Bouchard, J.、Frechet, J. M. J.、Willson, C. G.

  DOI：——

  日期：——