6,12-dioxatetradecanoic acid | 131178-87-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6,12-dioxatetradecanoic acid
• 英文别名: 5-(5-ethoxypentoxy)pentanoic acid
• CAS: 131178-87-5
• 化学式: C₁₂H₂₄O₄
• 分子量: 232.32
• InChiKey: YCZAFXIYWFGCNI-UHFFFAOYSA-N

物化性质

• 沸点：
  128-132 °C(Press: 0.1 Torr)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-戊二醇 在 吡啶 、 sodium dichromate 、 硫酸 、 水 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 87.0h， 生成 6,12-dioxatetradecanoic acid
  参考文献：
  名称：

  Nucleophile-dependent substitution reactions of 5-halovaleric acid esters: synthesis of 6,12-dioxamyristic acid

  摘要：

  The reaction of 5-ethoxypentan-1-ol with a variety of 5-halovalerate alkyl esters afforded ester exchange products rather than the expected products of Williamson ether synthesis. The virtually unknown reaction of an alkoxide with a 5-halovalerate ester contrasts strongly with literature reports of reactions involving other nucleophiles in which the halogen substitution products are nearly always isolated. An explanation is offered for this behavior in terms of a chelation-induced conformation of the substrate. Although the direct synthetic approach failed, the hitherto unknown title compound could still be prepared, albeit in six steps in 6% overall yield. The approach used is discussed along with the interesting chemistry of this system.

  DOI：

  10.1021/jo00002a046

文献信息

• Novel fatty acid analog enzyme substrates
  申请人：Washington University

  公开号：US05082967A1

  公开（公告）日：1992-01-21

  Novel diheteroatom-substituted fatty acid analog substrates of myristoylating enzymes are provided which contain oxyen and/or sulfur in place of two methylene groups in carbon positions from 3 to 13 in the fatty acid chain of a C.sub.13 -C.sub.14 fatty acid analog or alkyl ester thereof in which said oxygen or sulfur atoms are separated by at least one methylene group.

  提供了一种新型的二杂原子取代肌醇酰化酶脂肪酸类似物底物，其中在碳3到碳13的脂肪酸链中，用氧和/或硫代替了两个亚甲基基团，该C.sub.13-C.sub.14脂肪酸类似物或其烷基酯中的氧或硫原子至少相隔一个亚甲基基团。
• Method of N-acylating peptide and proteins with diheteroatom substituted
  申请人：Washington University

  公开号：US05571689A1

  公开（公告）日：1996-11-05

  A method for acylating peptides and proteins with the CoA-ester of diheteroatom substituted C.sub.13 to C.sub.14 myristic acid analogs catalyzed by N-myristoyltransferase is presented. In the analogs, two non-adjacent methylene groups, which are normally at positions 3-13, are replaced with oxygen or sulfur atoms.

  本文介绍了一种使用N-肉豆蔻酰转移酶催化的双杂原子取代C.sub.13至C.sub.14肉豆蔻酸酯的酰化肽和蛋白质的方法。在这些类似物中，通常位于3-13位的两个非相邻的亚甲基基团被氧或硫原子取代。
• KATOH, AKIRA;LU, TIANBAO;DEVADAS, B.;ADAMS, STEVEN P.;GORDON, JEFFREY I.;+, J. ORG. CHEM., 56,(1991) N, C. 731-735
  作者：KATOH, AKIRA、LU, TIANBAO、DEVADAS, B.、ADAMS, STEVEN P.、GORDON, JEFFREY I.、+

  DOI：——

  日期：——
• US5082967A
  申请人：——

  公开号：US5082967A

  公开（公告）日：1992-01-21
• US5571689A
  申请人：——

  公开号：US5571689A

  公开（公告）日：1996-11-05