dl-2,3-Di-tert-butylbernsteinsaeure

• 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: dl-2,3-Di-tert-butylbernsteinsaeure
• 英文别名: (+/-)-α,α'-di-tert-butylsuccinic acid；racem.-2,3-di-tert-butyl-succinic acid；racem.-2,3-Di-tert-butyl-bernsteinsaeure；(2S,3S)-2,3-ditert-butylbutanedioic acid
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: NCJIQZHBJMQVHD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dl-2,3-Di-tert-butylbernsteinsaeure 以 水 为溶剂， 生成 (+/-)-α,α'-di-tert-butylsuccinic anhydride
  参考文献：
  名称：

  Cyclic anhydrides. III. Equilibrium constants for the acid-anhydride equilibrium in aqueous solutions of certain vicinal diacids

  摘要：

  DOI：

  10.1021/ja00751a040
• 作为产物：
  描述：

  (+/-)-α,α'-di-tert-butylsuccinic anhydride 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 以94%的产率得到dl-2,3-Di-tert-butylbernsteinsaeure
  参考文献：
  名称：

  (±)-α,α'-二叔丁基琥珀酸酯的单阴离子中“最强”OHO氢键的不对称性

  摘要：

  (+/-)-alpha,alpha'-di-tert-butylsuccinic acid 的第一次和第二次去质子化之间的大 pK(a) 差异被解释为单阴离子中短而强的分子内氢键的证据。将 (18)O 并入一个羧基可以通过同位素扰动方法研究溶液中 H 键的对称性。相对于在二酸中测量的羧基碳上固有的 (18) O 诱导的同位素位移，观察到额外的同位素位移在甲醇中为 8 ppb，在丙酮中为 14 ppb，在 THF 中为 5 ppb 的氢钾 (+ /-)-α,α'-琥珀酸二叔丁酯-(18)O。这种增加表明离子作为相互转化互变异构体的平衡对存在，而不是作为单个对称共振杂化物存在。四丙基铵的X射线晶体结构，四丁基铵、四丁基鏻、镁和氢钙 (+/-)-α,α'-二叔丁基琥珀酸盐显示出非常短的 OO 距离，为 2.41 A，与强氢键一致。然而，(+/-)-α,α'-二叔丁基琥珀酸二阴离子的二铯盐也显示出

  DOI：

  10.1021/ja905806h

文献信息

• Benzodiazepines and anterior pituitary function
  作者：E. Arvat、R. Giordano、S. Grottoli、E. Ghigo

  DOI：10.1007/bf03345110

  日期：2002.9

  Benzodiazepines (BDZ) are one of the most prescribed classes of drugs because of their marked anxiolytic, anticonvulsant, muscle relaxant and hypnotic effects. The pharmacological actions of BDZ depend on the activation of 2 specific receptors. The central BDZ receptor, present in several areas of the central nervous system (CNS), is a component of the GABA-A receptor, the activation of which increases GABAergic neurotransmission and is followed by remarkable neuroendocrine effects. The peripheral benzodiazepine receptors (PBR), structurally and functionally different from the GABA-A receptor, have been shown in peripheral tissues but also in the CNS, in both neurones and glial cells, and in the pituitary gland. BDZ receptors bind to a family of natural peptides called endozepines, firstly isolated from neurons and glial cells in the brain and then in several peripheral tissues as well. Endozelpines modulate several central and peripheral biological activities, including some neuroendocrine functions and synthetic BDZ are likely to mimic them, at least partially. BZD, especially alprazolam (AL), possess a clear inhibitory influence on the activity of the HPA axis in both animals and humans. This effect seems to be mediated at the hypothalamic and/or suprahypothalamic level via suppression of CRH. The strong negative influence of AL on hypothalamic-pituitary-adrenal (HPA) axis agrees with its peculiar efficacy in the treatment of panic disorders and depression. BZD have also been shown to increase GH secretion via mechanisms mediated at the hypothalamic or supra-hypothalamic level, though a pituitary action cannot be ruled out. Besides the impact on HPA and somatotrope function, BDZ also significantly affect the secretion of other pituitary hormones, such as gonadotropins and. PRL, probably acting through GABAergic mediation in the hypothalamus and/or in the pituitary gland. In all, BDZ are likely to represent a useful tool to investigate GABAergic activity and clarify its role in the neuroendocrine control of anterior pituitary function; their usefulness probably overrides what had been supposed before.
• Cyclic anhydrides. III. Equilibrium constants for the acid-anhydride equilibrium in aqueous solutions of certain vicinal diacids
  作者：L. Eberson、H. Welinder

  DOI：10.1021/ja00751a040

  日期：1971.11
• Asymmetry of the “Strongest” OHO Hydrogen Bond, in the Monoanion of (±)-α,α′-Di-<i>tert</i>-butylsuccinate
  作者：Charles L. Perrin、Jonathan S. Lau、Yeong-Joon Kim、Phaneendrasai Karri、Curtis Moore、Arnold L. Rheingold

  DOI：10.1021/ja905806h

  日期：2009.9.23

  distance of 2.41 A, consistent with a strong hydrogen bond. However, the dicesium salt of the (+/-)-alpha,alpha'-di-tert-butylsuccinate dianion also shows the short O-O distance of 2.41 A, so this cannot be taken as evidence for a strong hydrogen bond in the monoanion. Moreover, the two O-H distances in the monoanions are unequal, and the hydrogen bond is asymmetric in these crystals. It is concluded

  (+/-)-alpha,alpha'-di-tert-butylsuccinic acid 的第一次和第二次去质子化之间的大 pK(a) 差异被解释为单阴离子中短而强的分子内氢键的证据。将 (18)O 并入一个羧基可以通过同位素扰动方法研究溶液中 H 键的对称性。相对于在二酸中测量的羧基碳上固有的 (18) O 诱导的同位素位移，观察到额外的同位素位移在甲醇中为 8 ppb，在丙酮中为 14 ppb，在 THF 中为 5 ppb 的氢钾 (+ /-)-α,α'-琥珀酸二叔丁酯-(18)O。这种增加表明离子作为相互转化互变异构体的平衡对存在，而不是作为单个对称共振杂化物存在。四丙基铵的X射线晶体结构，四丁基铵、四丁基鏻、镁和氢钙 (+/-)-α,α'-二叔丁基琥珀酸盐显示出非常短的 OO 距离，为 2.41 A，与强氢键一致。然而，(+/-)-α,α'-二叔丁基琥珀酸二阴离子的二铯盐也显示出