6-TBDPO-1-hexyl acetate | 156480-40-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 6-TBDPO-1-hexyl acetate
• 英文别名: 6-[Tert-butyl(diphenyl)silyl]oxyhexyl acetate
• CAS: 156480-40-9
• 化学式: C₂₄H₃₄O₃Si
• 分子量: 398.618
• InChiKey: SPJSGPBCPSXYNB-UHFFFAOYSA-N

物化性质

• 沸点：
  450.7±37.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• 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：

  6-TBDPO-1-hexyl acetate 在 dibutylstannanediyl bis(trifluoromethanesulfonate) lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 2-<5-(tert-Butyldiphenylsiloxy)pentan-1-yl>-1,3-dithiane
  参考文献：
  名称：

  Differentiation between carbonyls and acetals in 1,3-dithiane and 1,3-dithiolane synthesis catalyzed by organotin triflates

  摘要：

  Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates. In these competition reactions, various types of carbonyls and acetals are differentiated. Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals. The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones. Conversely, an aromatic acetal is more reactive than its parent aldehyde. In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates. However, aromatic acetals react preferentially over aliphatic acetals. Ketones of different types are also differentiated. No such discrimination can be achieved by conventional methods. Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals. Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.

  DOI：

  10.1021/jo00070a038
• 作为产物：
  描述：

  乙酰溴 、 1-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)hexane 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到6-TBDPO-1-hexyl acetate
  参考文献：
  名称：

  A one-step and chemoselective conversion of silyl-protected alcohols into the corresponding acetates

  摘要：

  A reagent system of acetyl bromide combined with a catalytic amount of tin(II) bromide cleaves readily trialkylsilyl ethers to give the corresponding acetates in high yields under very mild conditions.

  DOI：

  10.1016/s0040-4039(00)73040-1

文献信息

• A Facile and Efficient One-Step Conversion of Alcohol Triphenylmethyl Ethers to the Corresponding Acetates
  作者：Takeshi Oriyama、Kumiko Kobayashi、Tsutomu Watahiki

  DOI：10.1055/s-2003-37641

  日期：——

  Alcohol triphenylmethyl (trityl) ethers were readily and efficiently transformed into the corresponding acetates by reaction with acetyl bromide. Triphenylmethyl ethers can also be transformed into the corresponding substituted acetates in high yields by the use of various substituted acetyl chlorides combined with sodium iodide.

  醇三苯甲基（三苯甲基）醚通过与乙酰溴反应容易且有效地转化为相应的乙酸酯。通过使用各种取代的乙酰氯与碘化钠结合，三苯甲基醚也可以高产率地转化为相应的取代乙酸酯。
• <i>N,N</i>-Diarylammonium Pyrosulfate as a Highly Effective Reverse Micelle-Type Catalyst for Hydrolysis of Esters
  作者：Yoshiki Koshikari、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1021/ol301290c

  日期：2012.6.15

  Reverse micelle-type N,N-diarylammonium pyrosulfate (3–5 mol %) efficiently catalyzes the hydrolysis of esters (up to 100 mmol scale) under organic solvent-free conditions. The present method is successfully applied to the hydrolysis of various esters without the decomposition of the base-sensitive moieties and without any loss of optical purity for α-heterosubstituted carboxylic acids.

  反胶束型N，N-焦硫酸二芳基铵（3-5摩尔％）在无有机溶剂的条件下有效催化酯的水解（最大100 mmol规模）。本方法成功地用于各种酯的水解，而没有碱敏感部分的分解，并且对于α-杂取代的羧酸没有任何光学纯度的损失。
• METHOD FOR PRODUCING CARBOXYLIC ACID AND ALCOHOL BY HYDROLYSIS OF ESTER
  申请人：National University Corporation Nagoya University

  公开号：EP2799422B1

  公开（公告）日：2018-02-14
• ZrCl4 as a mild and efficient catalyst for the one-pot conversion of TBS and THP ethers to acetates
  作者：Ch.Sanjeeva Reddy、G Smitha、S Chandrasekhar

  DOI：10.1016/s0040-4039(03)01078-5

  日期：2003.6

  A mild, efficient and chemoselective method has been developed for the direct transformation of tert-butyldimethylsilyl and tetrahydropyranyl protected alcohols into the corresponding acetates with acetic anhydride and zirconium(IV) chloride as the catalyst in acetonitrile, in a one-pot reaction with high yields and short reaction times. This method has been applied to a variety of substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Oriyama Takeshi, Oda Mihoko, Gono Junko, Koga Gen, Tetrahedron Lett, 35 (1994) N 13, S 2027-2030
  作者：Oriyama Takeshi, Oda Mihoko, Gono Junko, Koga Gen

  DOI：——

  日期：——