12-(tert-butyldimethylsilyloxy)octadecanoic acid | 87042-44-2

• 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: 12-(tert-butyldimethylsilyloxy)octadecanoic acid
• 英文别名: 12-[tert-butyl(dimethyl)silyl]oxyoctadecanoic acid
• CAS: 87042-44-2
• 化学式: C₂₄H₅₀O₃Si
• 分子量: 414.745
• InChiKey: UXJQXWHCLNGHQI-UHFFFAOYSA-N

物化性质

• 沸点：
  474.7±18.0 °C(Predicted)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-(tert-butyldimethylsilyloxy)octadecanoic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6
• 作为产物：
  描述：

  4-[4-(乙酰基氨基)苯胺基]-1-氨基-9,10-二氢-9,10-二羰基蒽-2,6-二磺基酸 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 sodium dichromate 、 硫酸 、 三氟化硼 、 溶剂黄146 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 85.33h， 生成 12-(tert-butyldimethylsilyloxy)octadecanoic acid
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6

文献信息

• Activation and synthetic applications of thiostannanes. Protection of carboxyl groups with α-methylcinnamyl alcohol as a means of chemodifferentiation and selective activation
  作者：Tsuneo Sato、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/s0040-4039(00)99169-x

  日期：1989.1

  α-Methylcinnamyl (MEC) esters are converted into parent carboxylic acids under mild conditions, various functions being tolerated including acetoxy, siloxy, MEM, and so on. Furthermore, MEC esters are transformed into other esters through CsF-promoted alkylation of intermediary organotin carboxylates.

  在温和的条件下，α-甲基肉桂基（MEC）酯可转化为母体羧酸，可耐受多种功能，包括乙酰氧基，甲硅烷氧基，MEM等。此外，MEC酯通过CsF促进的中间有机锡羧酸酯的烷基化转化为其他酯。
• Amide derivatives and dermatologic preparations containing the same
  申请人：Kao Corporation

  公开号：US05221757A1

  公开（公告）日：1993-06-22

  An amide derivative represented by the following general formula (II): ##STR1## (wherein R.sup.3 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group carrying 10 to 40 carbon atoms; R.sup.4 represents a straight-chain or branched hydrocarbon group carrying 3 to 39 carbon atoms; and R.sup.5 represents a hydrogen atom, a straight-chain or branched, saturated or unsaturated hydrocarbon group carrying 10 to 40 carbon atoms or an acyl group); and a dermatologic preparation containing the same.

  一种由下列通式（II）表示的酰胺衍生物：##STR1##（其中R.sup.3代表具有10至40个碳原子的直链或支链、饱和或不饱和的碳氢基团；R.sup.4代表具有3至39个碳原子的直链或支链碳氢基团；R.sup.5代表氢原子、具有10至40个碳原子的直链或支链、饱和或不饱和的碳氢基团或酰基）；以及包含该化合物的皮肤学制剂。
• SATO, TSUNEO;OTERA, JUNZO;NOZAKI, HITOSI, TETRAHEDRON LETT., 30,(1989) N2, C. 2959-2962
  作者：SATO, TSUNEO、OTERA, JUNZO、NOZAKI, HITOSI

  DOI：——

  日期：——
• Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom
  作者：Lars Negelmann、Sandra Pisch、Uwe Bornscheuer、Rolf D Schmid

  DOI：10.1016/s0009-3084(97)00085-6

  日期：1997.11

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.