2-oxoheptadecanoic acid | 73506-86-2

• 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: 2-oxoheptadecanoic acid
• 英文别名: 2-Oxo-heptadecanoic acid
• CAS: 73506-86-2
• 化学式: C₁₇H₃₂O₃
• 分子量: 284.439
• InChiKey: QPDMNFFZLIUVIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxoheptadecanoic acid 在 盐酸 、 乙醇 、 zinc/copper couple 、 苯 作用下， 生成 2-hydroxy-2-pentadecyl-succinic acid diethyl ester
  参考文献：
  名称：

  Asano; Tamemasa, Yakugaku Zasshi, 1943, vol. 63, p. 375

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 溶剂黄146 作用下， 生成 2-oxoheptadecanoic acid
  参考文献：
  名称：

  Treatment with diazoxide causes prolonged improvement of β-cell function in rat islets transplanted to a diabetic environment

  摘要：

  Prolonged hyperglycemia desensitizes beta cells. A role for hyperglycemia-induced excessive stimulation can be tested by diazoxide, which inhibits glucose-induced insulin secretion. Using diazoxide, we have investigated in a rat transplantation model whether excessive stimulation can induce lasting effects on beta cells. One batch with 150 islets and another with 20 islets isolated from Wistar-Furth rats were transplanted under the left-kidney capsule of syngeneic streptozotocin-diabetic recipients. In a first series, recipients were treated for 8 weeks with or without 0.2% diazoxide in the food. Graft-bearing kidneys were then perfused and excised. Diazoxide treatment increased by 5.5;fold the insulin response to 10 mmol/L arginine, by 4.1-fold the graft insulin content, and by 2.3-fold the preproinsulin mRNA versus nontreated diabetic controls. The persistence of these effects was assessed in a second series in which 8 weeks of diazoxide treatment was followed by 1 week of no treatment. Again, perfusion experiments showed a higher insulin response to arginine in diazoxide-treated rats (136.0 +/- 25.7 v 62.3 +/- 11.8 fmol/min, P < .05). Also, the response to 27.8 mmol/L glucose was increased (54.0 +/- 17.1 v 13.6 +/- 7.8 fmol/min, P < .05). The insulin content was increased (2.2 +/- 0.6 v 1.0 +/- 0.4 pmol/islet, P < .05), as well as the preproinsulin mRNA (0.60 +/- 0.08 v 0.22 +/- 0.02 pg/islet, P < .05). In a third series, we tested the impact of diazoxide treatment when given only during the first 2 weeks following transplantation. When tested 6 weeks later, insulin secretion was unaffected, whereas there was a strong tendency for a higher preproinsulin mRNA and insulin content in grafts of diazoxide;treated rats. In conclusion, this study demonstrates that beta-cell function in transplanted islets is improved by diazoxide long after the end of treatment, an effect that is likely due to removal of hyperglycemia induced excessive stimulation. Copyright (C) 2000 by W.B. Saunders Company.

  DOI：

  10.1016/s0026-0495(00)80044-x

文献信息

• Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur
  作者：Masato Saito、Sho Murakami、Takeshi Nanjo、Yusuke Kobayashi、Yoshiji Takemoto

  DOI：10.1021/jacs.0c03256

  日期：2020.5.6

  for the thioacylation of amines using α-ketoacids and elemental sulfur has been developed. The key to success for this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties are tolerated under the applied reaction conditions. To demonstrate

  已经开发了一种使用 α-酮酸和元素硫对胺进行硫代酰化的温和且化学选择性的方法。这种转化成功的关键是硫醇（如 1-十二烷硫醇）对元素硫的亲核活化。在所应用的反应条件下，可以耐受各种官能团，包括未保护的羟基、羧基、酰胺、硫化物和叔胺部分。为了证明与使用 Lawesson 试剂或 P2S5 的传统 OS 交换反应相比，该方法的优势，将硫代酰胺部分特定地引入到生物活性化合物中。
• A Hydroperoxide‐Mediated Decarboxylation of α‐Ketoacids Enables the Chemoselective Acylation of Amines
  作者：Takeshi Nanjo、Natsuki Kato、Xuan Zhang、Yoshiji Takemoto

  DOI：10.1002/chem.201904717

  日期：2019.12.5

  decarboxylative amidation of α-ketoacids by using inexpensive tert-butyl hydroperoxide (TBHP), which is characterized by high yields, a broad substrate scope, mild reaction conditions, and a unique chemoselectivity. These features enable the synthesis of peptides from amino acid derived α-ketoacids under preservation of the stereochemical information.

  迄今为止，酰胺键形成的策略，即有机合成中最基本和最重要的转变之一，主要集中在脱水反应上。在本文中，我们报告并证明了通过使用廉价的叔丁基氢过氧化物（TBHP）来生产α-酮酸的新型脱羧酰胺化技术的实用性，该技术的特点是收率高，底物范围宽，反应条件温和以及独特的化学选择性。这些特征使得能够在保留立体化学信息的情况下从氨基酸衍生的α-酮酸合成肽。
• Photocatalytic Activation of Elemental Sulfur Enables a Chemoselective Three-Component Thioesterification
  作者：Sho Murakami、Takeshi Nanjo、Yoshiji Takemoto

  DOI：10.1021/acs.orglett.1c02904

  日期：2021.10.1

  thioesterification using olefins, α-ketoacids, and elemental sulfur has been developed. The photocatalytic activation of elemental sulfur, a cheap and abundant sulfur source, enables the rapid installation of a sulfur atom into molecules, reactions that ordinarily would require the use of reactive and malodorous sulfur-containing compounds such as thiols and thioacids. This novel reaction is characterized

  已经开发出使用烯烃、α-酮酸和元素硫的温和且化学选择性的三组分硫酯化反应。元素硫的光催化活化是一种廉价且丰富的硫源，能够将硫原子快速安装到分子中，而这些反应通常需要使用反应性和恶臭的含硫化合物，如硫醇和硫代酸。这种新反应的特点是产量高，底物范围广，可以将硫酯部分引入复杂的分子中，包括类固醇、肽和未受保护的糖苷。机理研究表明，这种转变的成功取决于元素硫所发挥的多种作用，包括硫化剂、末端氧化剂和 HAT 介质。
• Rapid Formation of Non‐canonical Phospholipid Membranes by Chemoselective Amide‐Forming Ligations with Hydroxylamines**
  作者：Jiyue Chen、Roberto J. Brea、Alessandro Fracassi、Christy J. Cho、Adrian M. Wong、Marta Salvador‐Castell、Sunil K. Sinha、Itay Budin、Neal K. Devaraj

  DOI：10.1002/anie.202311635

  日期：2024.1.2

  Bioorthogonal de novo phospholipid synthesis utilizing the reactions between hydroxylamine and α-ketoacids (KAs) or potassium acyltrifluoroborates (KATs) enables the rapid formation of biomimetic membranes under physiological pH conditions, using reactant concentrations in the micromolar range. Additionally, these reactions are biocompatible and can be performed in living mammalian cells.

  利用羟胺与α-酮酸 （KA） 或酰基三氟硼酸钾 （KAT） 之间的反应进行生物正交从头磷脂合成，能够在生理 pH 条件下使用微摩尔范围内的反应物浓度快速形成仿生膜。此外，这些反应具有生物相容性，可以在活的哺乳动物细胞中进行。
• Schreiber, Bulletin de la Societe Chimique de France, 1956, p. 1361
  作者：Schreiber

  DOI：——

  日期：——