tert-butyl 2-(2-methoxyethoxymethyl)acrylate | 133208-86-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 2-(2-methoxyethoxymethyl)acrylate
• 英文别名: tert-butyl 2-(2-methoxyethoxymethyl)prop-2-enoate
• CAS: 133208-86-3
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: QWYYMLRHVCXEGV-UHFFFAOYSA-N

物化性质

• 沸点：
  269.7±25.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(2-methoxyethoxymethyl)acrylate 在 碘 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 生成 sodium;1-[2-(2-methoxyethoxymethyl)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]cyclopentane-1-carboxylate
  参考文献：
  名称：

  Large-Scale Candoxatril Asymmetric Hydrogenation

  摘要：

  Ruthenium-catalyzed asymmetric hydrogenation was used to prepare tons of a key chiral succinate intermediate for clinical trials quantities of candoxatril. MeOBiphep was used as the ligand, and the catalyst was generated in situ from RuCOD-Bismethylallyl. THF was the best cosolvent for the reaction leading to a selective hydrogenation and a process which was readily amenable on large scale.

  DOI：

  10.1021/op010005w
• 作为产物：
  描述：

  甲基丙烯酸叔丁酯 在 碘 、 potassium carbonate 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 38.25h， 生成 tert-butyl 2-(2-methoxyethoxymethyl)acrylate
  参考文献：
  名称：

  Stereoselective synthesis of a candoxatril intermediate asymmetric hydrogenation

  摘要：

  A four step synthesis of a chiral glutarate half ester intermediate, required for the preparation of candoxatril, has been developed from t-butyl acrylate. The key steps in this route include a stereoselective synthesis of a trisubstituted alkene and its asymmetric hydrogenation with a Ru-BINAP catalyst. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02687-2

文献信息

• THE SYNTHESIS OF<i>GEM</i>-CYCLOPENTYL SUBSTITUTED GLUTARATES VIA THE OXIDATIVE RING CONTRACTION OF 2-ACETYLCYCLOHEXANONES
  作者：Stephen Challenger、Andrew Derrick、Terry V. Silk

  DOI：10.1081/scc-120012979

  日期：2002.1

  ABSTRACT A two step synthesis of differentially protected gem-cyclopentyl glutarates has been developed from 2-acetylcyclohexanone and acrylates. The key step involves an oxidative ring contraction reaction with hydrogen peroxide. The methodology has been used to prepare intermediates used in the preparation of the atriopeptidase inhibitor candoxatril.

  摘要 已经从 2-乙酰环己酮和丙烯酸酯开发了一种两步法合成受差别保护的 gem-环戊基戊二酸酯。关键步骤涉及与过氧化氢的氧化缩环反应。该方法已用于制备用于制备四肽酶抑制剂坎多沙曲的中间体。
• Preparation of glutaric acid derivatives
  申请人：Pfizer Inc.

  公开号：US05166406A1

  公开（公告）日：1992-11-24

  The invention provides a process for preparing a compound of the formula: ##STR1## or a base salt thereof, wherein R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by up to 3 substituents each independently selected from the group consisting of C.sub.1 -C.sub.6 alkoxy and C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6 alkoxy)-; and R.sup.3 is C.sub.1 -C.sub.6 alkyl or benzyl, said benzyl group being optionally ring-substituted by up to 2 nitro or C.sub.1 -C.sub.4 alkoxy substituents comprising reacting a compound of the formula: ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl or C.sub.1 -C.sub.4 alkoxy; and R.sup.2 and R.sup.3 are as previously defined for a compound of the formula (I), with hydrogen peroxide or a source of peroxide ions: said process being optionally followed by conversion of the compound of the formula (I) to a base salt thereof. The present invention also relates to novel compounds of the formula (II).

  该发明提供了一种制备下式化合物的过程：##STR1##或其相应的碱盐，其中R.sup.2是氢或C.sub.1-C.sub.6烷基，可选地被高达3个取代基取代，每个取代基独立地选自C.sub.1-C.sub.6烷氧基和C.sub.1-C.sub.6烷氧基(C.sub.1-C.sub.6烷氧基)-；和R.sup.3是C.sub.1-C.sub.6烷基或苄基，所述苄基可选地被高达2个硝基或C.sub.1-C.sub.4烷氧基取代基取代，包括将下式化合物与过氧化氢或过氧化物离子源反应：##STR2##其中R.sup.1是C.sub.1-C.sub.4烷基、苯基或苄基或C.sub.1-C.sub.4烷氧基；而R.sup.2和R.sup.3如前所述定义为上述式(I)的化合物，随后可选择性地将式(I)的化合物转化为其相应的碱盐。本发明还涉及新的式(II)化合物。
• Hydrogenation
  申请人：Pfizer Inc.

  公开号：US05618970A1

  公开（公告）日：1997-04-08

  Compounds of formula ##STR1## where R is 5-indanyl or a carboxylic acid protecting group, or an amine salt thereof, are prepared by hydrogenating an (E)-allylic ether of formula ##STR2## in the presence of a stereoselective rhodium or ruthenium biphosphine catalyst and a protic solvent.

  式为##STR1##的化合物，其中R为5-吲哚基或羧酸保护基，或其氨盐，可通过在立体选择性的铑或钌双膦催化剂和质子溶剂的存在下，加氢式为##STR2##的(E)-烯丙基醚来制备。
• US5166406A
  申请人：——

  公开号：US5166406A

  公开（公告）日：1992-11-24
• US5618970A
  申请人：——

  公开号：US5618970A

  公开（公告）日：1997-04-08