(+)-(S)-hexadecane-1,3-diol | 114634-28-5

• 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: (+)-(S)-hexadecane-1,3-diol
• 英文别名: (3S)-hexadecane-1,3-diol
• CAS: 114634-28-5
• 化学式: C₁₆H₃₄O₂
• 分子量: 258.445
• InChiKey: GZXNLYGAGAVUSB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  14
• 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：

  (+)-(S)-hexadecane-1,3-diol 在 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 sodium acetate 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.75h， 生成 (S)-5-Benzyloxy-2,2-dimethyl-octadecan-3-ol
  参考文献：
  名称：

  [1,3]-在尼古拉斯反应过程中，在γ-苄氧基炔丙醇中的手性转移。

  摘要：

  描述了高度区域和立体选择性的分子内[1,5]-氢转移过程。用BF3 x OEt2处理γ-苄基保护的Co2（CO）6-α，γ-炔二醇可提供双均炔丙基醇。反应在几秒钟内发生，可耐受多种功能，并提供良好的收率。当醚基位于立体化学定义的碳原子上时，重排会以高立体选择性发生，从而将甲醇中心的手性转移至新创建的立体中心。当存在另外的苄基醚时，苄氧基的裂解是完全区域选择性的。评价了该新方法在密集取代的底物中的范围和局限性，还描述了可能的竞争反应和/或立体化学影响。

  DOI：

  10.1002/chem.200501127
• 作为产物：
  描述：

  3-氧代十六烷酸甲酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 二异丁基铝-2,6-二-叔丁基-4-羟基甲苯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 43.5h， 生成 (+)-(S)-hexadecane-1,3-diol
  参考文献：
  名称：

  Enantioselective construction of heterocycles. Synthesis of (R,R)-solenopsin B

  摘要：

  DOI：

  10.1021/jo00248a013

文献信息

• Structure Revision of a Widespread Marine Sulfonolipid Class Based on Isolation and Total Synthesis
  作者：Dávid Roman、Philippe Meisinger、Richard Guillonneau、Chia‐Chi Peng、Lukas K. Peltner、Paul M. Jordan、Veit Haensch、Sebastian Götze、Oliver Werz、Christian Hertweck、Yin Chen、Christine Beemelmanns

  DOI：10.1002/anie.202401195

  日期：——

  The planar structure of a newly reported group of bacterial sulfur-containing aminolipids was revised and their absolute configuration determined by a combination of analytical techniques, isolation, degradation experiments, and total synthesis. The revised structures, termed cysteinolides, diverge from previous homotaurine-based proposals, revealing a composition of a cysteinolic acid containing head

  对新报道的一组细菌含硫氨基脂的平面结构进行了修改，并通过分析技术、分离、降解实验和全合成的结合确定了它们的绝对构型。修改后的结构被称为半胱氨酸内酯，与之前基于同牛磺酸的提议不同，揭示了含有被各种（α-羟​​基）羧酸酰化的头基的半胱氨酸的组成。
• Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction
  作者：Linli He、Meni Wanunu、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/jo9906375

  日期：1999.8.1

  A one-pot regio- and stereospecific azidation reaction of 1,2- and 1,3-diols with azidotrimethylsilane (Me3SiN3) via a Mitsunobu reaction has been achieved. With 1,2- and 1,3-diols, the reaction of triphenylphosphine, diisopropyl azodicarboxylate, and Me3SiN3 in dichloromethane gave regioselective azidation at C-2 and C-3, respectively, in good yield (74-90% combined yield of 1a + 1b or of 2a + 2b). However, application of the same reaction conditions to a 1,4-diol led to the exclusive formation of the cyclic ether. The regioselectivity of this one-pot reaction is influenced by the solvent, the degree of steric bulk at C-2 of the 1,2-diol or at C-3 of the 1,3-diol, and the presence of electron-donating and electron-withdrawing groups near the secondary carbinol carbon. This selectivity is discussed in terms of the mechanistic model proposed by Mathieu-Pelta and Evans (Mathieu-Pelta, I.; Evans, S. A., Jr. J. Org. Chem. 1898, 57, 3409-3413), which involves reaction of the dioxaphospholane intermediate with Me3SiN3 to form oxyphosphonium ions 4 and 5.
• The synthesis of pseudomycin C′ via a novel acid promoted side-chain deacylation of pseudomycin A
  作者：Michael J Rodriguez、Matthew Belvo、Robert Morris、Douglas J Zeckner、William L Current、Roberta K Sachs、Mark J Zweifel

  DOI：10.1016/s0960-894x(00)00613-2

  日期：2001.1

  The gamma hydroxyl present in the aliphatic side chain of the natural products pseudomycin A and C' provided a unique handle for the pH dependent side-chain deacylation. Low pH reaction conditions were used to cleave the side chain with minimal degradation of the peptide core. The pseudomycin nucleus intermediate obtained from the deacylation of pseudomycin A was pivotal in the synthesis of novel side-chain analogues. A practical synthesis of a minor fermentation factor pseudomycin C' and related analogues is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enantiocontrolled Synthesis of Trialkyl-Substituted Stereogenic Carbons. A General Route to <i>cis-</i>3,5-Dialkyl γ-Lactones
  作者：David Díaz、Víctor S. Martín

  DOI：10.1021/ol991287b

  日期：2000.2.1

  [GRAPHICS]Lewis acid treatment of tertiary Co-2(CO)(6)-propargylic alcohols having a stereochemically defined benzyloxy group at the gamma-benzyl position yielded after cobalt demetalation sec-dialkyl bishomopropargylic alcohols in good yields. The reaction is highly stereoselective and predictable, providing pure stereoisomers. The use of benzyl-alpha,alpha'-d(2) ethers permitted the stereoselective d-labeling of methines and methylenes, Very simple chemical manipulations provided a general methodology to obtain the enantiomers of 3,5-dialkyl-gamma-lactones.
• TABER, DOUGLASS F.;DEKER, P. BRUCE;FALES, HENRY M.;JONES, TAPPEY H.;LLOYD+, J. ORG. CHEM., 53,(1988) N 13, 2968-2971
  作者：TABER, DOUGLASS F.、DEKER, P. BRUCE、FALES, HENRY M.、JONES, TAPPEY H.、LLOYD+

  DOI：——

  日期：——