[1,1,10,10-2H4]-decane-1,10-diol | 67986-07-6

• 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: [1,1,10,10-2H4]-decane-1,10-diol
• 英文别名: decane-1,1,10,10-d4-1,10-diol；1,1,10,10-Tetradeuteriodecan-1,10-diol；1,1,10,10-tetradeuterio-decane-1,10-diol；1,1,10,10-Tetradeuteriodecane-1,10-diol
• CAS: 67986-07-6
• 化学式: C₁₀H₂₂O₂
• 分子量: 178.252
• InChiKey: FOTKYAAJKYLFFN-YQUBHJMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1,1,10,10-2H4]-decane-1,10-diol 在 Bromotris(Triphenylphosphine)Rhodium(I) 正丁基锂 、 Dowex 50 W H⁺ form 、 氨 、 氢溴酸 、 氢气 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 24.5h， 生成 [1,10,10-2H3]-hexadecanal
  参考文献：
  名称：

  Biosynthesis of sex pheromones in moths: stereochemistry of fatty alcohol oxidation in Manduca sexta

  摘要：

  Six chiral deuterium labelled metabolic probes, (R) and (S)-enantiomers of [1, 10, 10-H-2(3)]-hexadecan-1-ol, (11E)-[1,10,10-H-2(3)]-hexadec-11-en-1-ol and (11Z)-[1, 10, 10-H-2(3)]-hexadec-11-en-1-ol, were synthesized to examine the stereospecificity of the fatty alcohol oxidase from the female pheromone gland of the tobacco hawk moth (Manduca sexta, Sphingidae). Both in vitro and in vivo oxidations were found to proceed by selective removal of the C1-H-R hydrogen or deuterium atom (Re-specificity) to yield the corresponding aldehydes. (R) and (S)-enantiomers of deuterium labelled salicyl alcohol and 2-thienyl-methanol, compounds entirely chemically diverse from the natural pheromone precursors, were also oxidised Re-specifically to salicylaldehyde and 2-thiophenecarb-aldehyde, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01199-7
• 作为产物：
  描述：

  1,10-癸二醇 在 5% activated charcoal-supported ruthenium catalyst 、 氢气 、 重水 作用下， 80.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以89%的产率得到[1,1,10,10-2H4]-decane-1,10-diol
  参考文献：
  名称：

  一种方便有效的区域选择性氘化方法

  摘要：

  通过在碳上使用5％钌（Ru / C），氢气和氧化氘（D 2 O）的组合，可以实现邻位碳上羟基的便捷和区域选择性氘化。

  DOI：

  10.1002/adsc.200800407

文献信息

• Ruthenium Catalyzed Deuterium Labelling of α-Carbon in Primary Alcohol and Primary/Secondary Amine in D₂O
  作者：Masaaki Takahashi、Koichiro Oshima、Seijiro Matsubara

  DOI：10.1246/cl.2005.192

  日期：2005.2

  Primary alcohols and primary/secondary amines are labelled with D atom at α-position regioselectively by means of deuterium oxide and ruthenium catalyst.

  伯醇和伯/仲胺通过氧化氘和钌催化剂在α位区域选择性地用D原子标记。
• A Reductive Deuteration Approach to the Efficient Synthesis of Deuterated Polymers
  作者：Yanhong Dong、Jie An、Lei Ning、Lijun Wang、Mengqi Peng、Zixuan Qin、Hengzhao Li、Shangzhong Liu

  DOI：10.1055/a-1796-7064

  日期：2022.5

  Deuterated polymers have wide applications but limited synthetic methods. In this study, we report an efficient two-step approach for the synthesis of deuterated polyesters and polyurethanes. Firstly, two practical single-electron transfer (SET) reductive-deuteration methods have been developed for site-selective introduction of C(sp3)–D into diol monomers. Nine deuterated diol monomers with high deuterium

  氘代聚合物应用广泛，但合成方法有限。在这项研究中，我们报告了一种有效的两步法合成氘代聚酯和聚氨酯。首先，已经开发了两种实用的单电子转移 (SET) 还原-氘化方法，用于将 C(sp 3 )-D 位点选择性引入二醇单体中。在 SmI 2 -D 2 O 和/或 Na-EtOD- d 1下合成了九种具有高氘掺入的氘化二醇单体SET 还原氘条件。然后，使用这些氘代单体在典型的聚合条件下合成了六种典型的氘代聚酯和聚氨酯。在所有合成的聚合物中，充分保持了高氘掺入，这展示了该方法在合成具有位点特异性氘标记的聚合物中的潜在应用。
• Biosynthesis of sex pheromones in moths: stereochemistry of fatty alcohol oxidation in Manduca sexta
  作者：Michal Hoskovec、Anna Luxová、Aleš Svatoš、Wilhelm Boland

  DOI：10.1016/s0040-4020(02)01199-7

  日期：2002.11

  Six chiral deuterium labelled metabolic probes, (R) and (S)-enantiomers of [1, 10, 10-H-2(3)]-hexadecan-1-ol, (11E)-[1,10,10-H-2(3)]-hexadec-11-en-1-ol and (11Z)-[1, 10, 10-H-2(3)]-hexadec-11-en-1-ol, were synthesized to examine the stereospecificity of the fatty alcohol oxidase from the female pheromone gland of the tobacco hawk moth (Manduca sexta, Sphingidae). Both in vitro and in vivo oxidations were found to proceed by selective removal of the C1-H-R hydrogen or deuterium atom (Re-specificity) to yield the corresponding aldehydes. (R) and (S)-enantiomers of deuterium labelled salicyl alcohol and 2-thienyl-methanol, compounds entirely chemically diverse from the natural pheromone precursors, were also oxidised Re-specifically to salicylaldehyde and 2-thiophenecarb-aldehyde, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A Convenient and Effective Method for the Regioselective Deuteration of Alcohols
  作者：Tomohiro Maegawa、Yuta Fujiwara、Yuya Inagaki、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/adsc.200800407

  日期：2008.10.6

  The convenient and regioselective deuteration of hydroxy groups on vicinal carbons was achieved by the combination of 5% ruthenium on carbon (Ru/C), hydrogen gas and deuterium oxide (D2O).

  通过在碳上使用5％钌（Ru / C），氢气和氧化氘（D 2 O）的组合，可以实现邻位碳上羟基的便捷和区域选择性氘化。