1-(4-methoxybenzyloxy)-5-trimethylsilanylpent-4-ol | 444809-41-0

• 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: 1-(4-methoxybenzyloxy)-5-trimethylsilanylpent-4-ol
• 英文别名: 1-(para-methoxybenzyloxy)-5-trimethylsilyl-4-pentyn-2-ol；1-[(4-Methoxyphenyl)methoxy]-5-trimethylsilylpent-4-yn-2-ol
• CAS: 444809-41-0
• 化学式: C₁₆H₂₄O₃Si
• 分子量: 292.45
• InChiKey: MBBGOBVNQKCCAB-UHFFFAOYSA-N

物化性质

• 沸点：
  384.9±42.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyloxy)-5-trimethylsilanylpent-4-ol 在 正丁基锂 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 tert-Butyl-[1-(4-methoxy-benzyloxymethyl)-pent-3-ynyloxy]-dimethyl-silane
  参考文献：
  名称：

  A study toward a total synthesis of fostriecin

  摘要：

  In order to synthesize the major C(3)-C(12) part of fostriecin, asymmetric dihydroxylation of several dienes 5a-f, prepared by cross-coupling reactions of several types. vas studied, thus providing high dependency on the hydroxyl groups at C(5) and C(l 1). The best regioselectivity was obtained with 5d to produce diol 23. which was later transformed into the advanced intermediate 26. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00403-3
• 作为产物：
  描述：

  4-甲氧基氯苄 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.74h， 生成 1-(4-methoxybenzyloxy)-5-trimethylsilanylpent-4-ol
  参考文献：
  名称：

  Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach

  摘要：

  Bestmann亚磷酰基[(三苯基磷氧基)酮烯]作为一种化学枢纽，将亲核实体，如醇或胺，与羰基部分连接起来，分别生成不饱和酯和酰胺。在这项工作中，通过Bestmann亚磷酰基、醇和α,β-不饱和醛的偶联实现了α,β,γ,δ-不饱和酯(二烯酸酯)的生成。一级和二级醇，包括烯丙基醇，都是合适的底物；新形成烯烃具有E-型几何结构。策略上，这代表了一条高效合成不饱和聚酮衍生物的路线。利用Bestmann亚磷酰基将C16-C20醇与C3-C8醛片段连接起来，研究了通过枢纽法合成天然产物zampanolide和dactylolide主要片段的方法。

  DOI：

  10.3762/bjoc.11.197

文献信息

• A Ru-Catalyzed Tandem Alkyne−Enone Coupling/Michael Addition:  Synthesis of 4-Methylene-2,6-<i>cis</i>-tetrahydropyrans
  作者：Barry M. Trost、Hanbiao Yang、Georg Wuitschik

  DOI：10.1021/ol0520065

  日期：2005.10.1

  [reaction: see text] A Ru-catalyzed tandem alkyne-enone coupling/Michael addition reaction is reported. It provides an efficient, atom-economic entry to 4-methylene-2,6-cis-tetrahydropyrans from simple, readily available homopropargylic alcohols and beta,gamma-unsaturated enones in good yields. Further functionalization of the resultant vinylsilane leads to the synthesis of either geometrically defined

  [反应：见正文]报告了Ru催化的串联炔烃-烯酮偶联/ Michael加成反应。它可以简单易得的均丙醇和β，γ-不饱和烯酮以高收率高效，原子经济地进入4-亚甲基-2,6-顺式四氢吡喃。所得乙烯基硅烷的进一步官能化导致在几何上限定于2,6-顺式-二氢吡喃外环的三取代烯烃的合成。
• Formation of Chiral C(sp³)−C(sp) Bond by Allylic Substitution of Secondary Allylic Picolinates and Alkynyl Copper Reagents
  作者：Yohei Kiyotsuka、Yuichi Kobayashi

  DOI：10.1021/jo901728b

  日期：2009.10.2

  To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine)CO2-, (2-pyrazine)CO2-, (EtO)(2)PO2-, C6F5CO2-, o-(Ph2P)-C6H4CO2-, MeOCO2-, or AcO-group were examined. First, picolinate (R-1 = Me, R-2 = CH2OPMB) was subjected to reaction with (TMS-C C)(2)CuLi center dot LiBr at 0 degrees C. Although no substitution took place, MgBr, (3 equiv) was found to promote the reaction to produce the anti S(N)2' product in 93% yield with 94% regioselectivity and 99% chirality transfer. In contrast, substitution of the other esters with the copper reagent in the presence of MgBr, were less reactive ((2-pyrazin)CO2-) or marginally reactive (other cases). Generality of the substitution using picolinates was established with five picolinates (R-1 = Me, Ph(CH2)(2), PMBO(CH2)(3); R-2 = Me, CH2OPMB, CH2OTBS, C5H11, c-C6H11) and seven alkynyl copper reagents (R-3 = TMS, Ph, p-TBSOC6H4, p- and o-MeOC6H4, P-MeC6H4, p-FC6H4), furnishing anti S(N)2' products in 61-93% yields with high regioselectivity (usually > 90%) and high chirality transfer (usually > 95%). In addition, transformation of the products was briefly studied.