<3,3-D2>stearic acid | 62689-93-4

• 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: <3,3-D2>stearic acid
• 英文别名: [3,3-D2]stearic acid
• CAS: 62689-93-4
• 化学式: C₁₈H₃₆O₂
• 分子量: 286.467
• InChiKey: QIQXTHQIDYTFRH-BPPAMHLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  20.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <3,3-D2>stearic acid 在 吡啶 、 五氯化磷 、 碳酸氢钠 作用下， 以 苯 为溶剂， 反应 20.0h， 生成 17β-estradiol-17-<3',3'-D2>stearate
  参考文献：
  名称：

  Mass spectrometric studies on 17β-estradiol-17-fatty acid esters: Evidence for the formation of anion-dipole intermediates

  摘要：

  AbstractThe behaviour towards low collision energy processes (eV range) of [M  H]− prepared under negative ion chemical ionization (NICI) ammonia conditions from 17β‐estradiol‐17‐fatty acid esters has been investigated. From such bifunctional compounds containing two acidic sites (i.e. phenol and ester groups), two isomeric forms (i.e. phenoxide and enolate forms) characterize the [M  H]− ion structures, whose distribution depends on the ion preparation mode. Here NICI (ammonia) provides both phenoxide and enolate forms as the [M  H]− species. This behaviour contrasts with the regioselectivity observed for proton abstraction from phenol under NICI (N2O) and fast atom bombardment conditions. Production of both phenoxide and enolate forms in NICI (ammonia) is demonstrated under NICI (ND3) conditions in which DO‐labelled [Md  H]− enolate ions are produced in a similar yield to unlabelled [Md  D]− phenoxide ions. Collisionally activated dissociation (CAD) spectra of both isomeric deprotonated molecules differ strongly by the presence of two different pairs of complementary daughter ions, suggesting that these ionic species are unconvertible. This is due to a steric hindrance effect on the long‐distance proton transfer. A mechanistic investigation on the formation of fragment ion pairs produced under CAD was performed with various deuterium‐labelled molecules. From these experiments, evidence is provided for molecular isomerizations into ion‐dipole complexes (prior to dissociation) which are structurally dependent on the initial charge location. Direct dissociation of these intermediates competes with the occurrence of exothermic proton transfer(s) yielding the formation of other isomeric intermediate forms. The orientation of these proton transfers is dictated by the relative acidities of both moieties of the complex.

  DOI：

  10.1002/oms.1210270612
• 作为产物：
  描述：

  hexadecan-1,1-d₂-1-ol 在 吡啶 、 氢氧化钾 、 氯化亚砜 、 sodium 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 <3,3-D2>stearic acid
  参考文献：
  名称：

  Mass spectrometric studies on 17β-estradiol-17-fatty acid esters: Evidence for the formation of anion-dipole intermediates

  摘要：

  AbstractThe behaviour towards low collision energy processes (eV range) of [M  H]− prepared under negative ion chemical ionization (NICI) ammonia conditions from 17β‐estradiol‐17‐fatty acid esters has been investigated. From such bifunctional compounds containing two acidic sites (i.e. phenol and ester groups), two isomeric forms (i.e. phenoxide and enolate forms) characterize the [M  H]− ion structures, whose distribution depends on the ion preparation mode. Here NICI (ammonia) provides both phenoxide and enolate forms as the [M  H]− species. This behaviour contrasts with the regioselectivity observed for proton abstraction from phenol under NICI (N2O) and fast atom bombardment conditions. Production of both phenoxide and enolate forms in NICI (ammonia) is demonstrated under NICI (ND3) conditions in which DO‐labelled [Md  H]− enolate ions are produced in a similar yield to unlabelled [Md  D]− phenoxide ions. Collisionally activated dissociation (CAD) spectra of both isomeric deprotonated molecules differ strongly by the presence of two different pairs of complementary daughter ions, suggesting that these ionic species are unconvertible. This is due to a steric hindrance effect on the long‐distance proton transfer. A mechanistic investigation on the formation of fragment ion pairs produced under CAD was performed with various deuterium‐labelled molecules. From these experiments, evidence is provided for molecular isomerizations into ion‐dipole complexes (prior to dissociation) which are structurally dependent on the initial charge location. Direct dissociation of these intermediates competes with the occurrence of exothermic proton transfer(s) yielding the formation of other isomeric intermediate forms. The orientation of these proton transfers is dictated by the relative acidities of both moieties of the complex.

  DOI：

  10.1002/oms.1210270612

文献信息

• Chemoenzymatic β-specific methylene C(sp³)–H deuteration of carboxylic acids
  作者：Xicheng Wang、Zhaohui Sun、Tao Li、Saima Perveen、Pengfei Li

  DOI：10.1039/d4gc00082j

  日期：——

  including borate, palladium, and lipase, enabled a one-pot β-specific methylene C(sp3)–H deuteration reaction of aliphatic acids using D2O. In the context of the widely used 8-aminoquinoline (8-AQ) directed C–H activation, this represented the first example of catalytic formation and cleavage of the directing group under mild conditions. Compared with previous deuteration methods, high chemo- and regioselectivity

  一锅中结合使用硼酸盐、钯和脂肪酶等三种催化剂，可利用 D 2 O实现脂肪酸的一锅 β 特异性亚甲基 C(sp 3 )–H 氘化反应。广泛使用的8-氨基喹啉（8-AQ）定向C-H活化，这是在温和条件下催化形成和裂解定向基团的第一个例子。与以前的氘化方法相比，在不使用强酸、强碱或缩合剂等环境友好试剂的情况下，获得了高化学和区域选择性、高产率和高氘化率。该方案还适用于 α,α,β,β-四氘代酸和各种氘代药物分子的合成。