2,2-Dihexadecyl-1,3-propanediol | 170025-80-6

• 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: 2,2-Dihexadecyl-1,3-propanediol
• 英文别名: 2,2-Dihexadecylpropane-1,3-diol
• CAS: 170025-80-6
• 化学式: C₃₅H₇₂O₂
• 分子量: 524.955
• InChiKey: WFNPNUWYCSEJME-UHFFFAOYSA-N

物化性质

• 沸点：
  616.8±28.0 °C(Predicted)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  37
• 可旋转键数：
  32
• 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：

  2,2-Dihexadecyl-1,3-propanediol 在 sodium hydroxide 、 硫酸 、 mercury dibromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Biological Activity of the Novel Sulfated and Phosphorylated Bivalent,.BETA.-D-Galactopyrano-sides Containing Fatty-Alkyl Residues.

  摘要：

  已经合成了新型硫酸化和磷酸化β-D-半乳糖苷二聚体，其中含有取代神经酰胺的脂肪烷基残基。在体外实验中，合成的糖脂对HL-60细胞与固定化的P、L和E选择素结合表现出有趣的抑制作用。这些糖脂可能作为有效的治疗剂，用于治疗选择素依赖性炎症。

  DOI：

  10.1248/cpb.45.1726
• 作为产物：
  描述：

  dihexadecylmalonic acid diethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2,2-Dihexadecyl-1,3-propanediol
  参考文献：
  名称：

  Synthesis of new lipophilic ortho-dicarboranes

  摘要：

  The synthesis of several new lipoidal dicarborane compounds prepares by reaction of decarborane with several fatty mono- and bis-alkyl-1,3-diols is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00870-3

文献信息

• Langmuir-blodgett film aggregates
  申请人：K & V LICENCING OY

  公开号：EP0284314A1

  公开（公告）日：1988-09-28

  A multilayered Langmuir-Blodgett film aggregate, which contains on top of a solid support surface several mo­nomolecular layers of a compound of liquid crystal type preferably having the general formula wherein Rʹ and Rʺ independently refer to a substantial­ly aliphatic hydrocarbon group of approximately 8 to 30 carbon atoms, Yʹ and Yʺ independently refer to the group -O-, -C(=O)-O-, which over the oxygen atom is bound to the group -(CH₂)n- or they refer to -CH₂-, nʹ and nʺ independently are zero or 1, R¹-X-H is a polar group wherein XH refers to hydroxy (OH), carboxyl (COOH), amino (NH₂), or an amino group substituted with a substantially aliphatic hydrocarbon group of not more than 30 carbon atoms, and R¹ is a direct bond, a carbonyl group -C(=O)-, lower alkylene or lower alkylene carboxyl lower alkylene, R² is hydrogen, lower alkyl or lower alko­xycarbonyl or has the meaning of R¹-X-H, or the meaning of Rʹ-Yʹ-(CH₂)nʹ-, provided that the compound (I) does not contain more than three lipophilic groups as defined.

  一种多层朗缪尔-布洛杰特薄膜聚合体，它在固体支撑表面上含有若干液晶类型化合物的单分子层，这些化合物最好具有通式 其中 Rʹ 和 Rʺ 独立地指大约 8 至 30 个碳原子的基本脂肪烃基，Yʹ 和 Yʺ 独立地指基团 -O-、-C(=O)-O-、R¹-X-H是极性基团，其中XH指羟基（OH）、羧基（COOH）、氨基（NH₂）、R¹是直接键、羰基-C(=O)-、低级亚烷基或低级亚烷基羧基低级亚烷基、R² 是氢、低级烷基或低级烷氧羰基，或具有 R¹-X-H 的含义，或具有 Rʹ-Yʹ-(CH₂)nʹ- 的含义，条件是化合物(I)不包含三个以上所定义的亲脂基团。
• Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Biological Activity of the Sulfated and Phosphorylated Multivalent β-D-Galactopyranosides Containing Fatty Alkyl Residues
  作者：Takao Ikami、Noboru Tomiya、Takashi Morimoto、Noriyuki Iwata、Reiko Yamashita、Takahito Jomori、Toshinao Usui、Yasuo Suzuki、Harunari Tanaka、Daisei Miyamoto、Hideharu Ishida、Akira Hasegawa、Makoto Kiso

  DOI：10.1080/07328309808002333

  日期：1998.5.1

  Ten sulfated and three phosphorylated beta-D-galactopyranoside dimers and one sulfated beta-D-galactopyranoside trimer containing fatty alkyl residues in place of ceramide have been synthesized. The coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide (2) with branched fatty alkyl diols and a triol (1a-1j) using mercury bromide as an activating agent gave the corresponding parent glycolipids (4a-4j) in good yields. Regioselective sulfation of these parent glycolipids through the dibutylstannylene acetals produced the target sulfated glycolipids, 3-sulfate (5a-5j) while stepwise phosphorylation with dibenzyloxy(diisopropylamino)phosphine gave the phosphorylated glycolipids, 3,4-bisphosphate (9e, g, i). The synthetic glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L- and E-selectin.