1,2-O-Isopropyliden-1,2-dihydroxyundecan-11-ol | 69380-63-8

• 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: 1,2-O-Isopropyliden-1,2-dihydroxyundecan-11-ol
• 英文别名: 4-(9-hydroxynonyl)-2,2-dimethyl-1,3-dioxolane；9-(2,2-dimethyl-1,3-dioxolan-4-yl)nonan-1-ol；2.2-Dimethyl-4-(9-hydroxynonyl)-dioxolan
• CAS: 69380-63-8
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: CTZMGBRWZBWADH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-O-Isopropyliden-1,2-dihydroxyundecan-11-ol 在 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以63%的产率得到4-(9-chlorononyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  使用O，S-缩醛，1,3-二溴-5,5-二甲基乙内酰脲和BHT从1,2-和1,3-二醇形成亚甲基乙缩醛

  摘要：

  描述了使用甲氧基甲基苯硫醚，1,3-二溴-5,5-二甲基乙内酰脲（DBDMH）和二丁基羟基甲苯（BHT）由1,2-和1,3-二醇形成亚甲基缩醛的温和有效方法。在该方法中使用BHT可抑制副反应，并能高产形成各种二醇（包括碳水化合物型底物）的亚甲基缩醛。

  DOI：

  10.1021/jo4000256
• 作为产物：
  描述：

  4-(9-methoxymethoxynonyl)-2,2-dimethyl-1,3-dioxolane 在 2,2'-联吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 15.0h， 以96%的产率得到1,2-O-Isopropyliden-1,2-dihydroxyundecan-11-ol
  参考文献：
  名称：

  Selective Deprotection of Methylene Acetal and MOM Ether in the Presence of Ketal-Type Protective Groups: Remarkable Effect of TBSOTf

  摘要：

  A novel procedure for highly selective deprotection of methylene acetals and MOM (methoxymethyl) groups in the presence of ketal-type protective groups has been developed. The method, which utilizes a combination of TBSOTf and 2,2'-bipyridyl, displays a completely opposite selectivity compared with those of acid-mediated deprotection protocols.

  DOI：

  10.3987/com-12-s(n)43

文献信息

• Synthesis and thermotropic liquid crystalline properties of calamitic molecules with laterally attached hydrophilic groups: Y-shaped three-block molecules which can form smectic and columnar mesophases
  作者：Rene Plehnert、Jörg Andreas Schröter、Carsten Tschierske

  DOI：10.1039/a803043j

  日期：——

  The synthesis and the thermotropic liquid crystalline properties of calamitic mesogens (p-terphenyl derivatives, a biphenyl and a p-quintaphenyl derivative) with a laterally attached hydrophilic group (1,2-diol groups, primary and secondary amides, polyether chains, crown ether units, carbohydrate units, a hydrazide, a quaternary ammonium salt, a carboxylic acid and a sodium carboxylate) are reported. The compounds were investigated by means of polarizing microscopy and calorimetry. The influence of the type of the polar group, of the length of the rigid core and the position of the connection of the hydrophilic group with the rod-like rigid core have been investigated. Many of these amphiphilic molecules can form monolayer S A phases. If a sufficient amount of hydrogen bonding is available their mesophase stability can be higher than that of related compounds with other lateral substituents. Rectangular columnar mesophases can be found for compounds with rather large and flexible polar lateral substituents (polyether chains) fixed to the center of the rigid terphenyl unit. These columnar phases should represent ribbon phases resulting from the collapse of the smectic layers (modulated smectic phases). The proposed model is also related to that suggested for supermolecular structures of triblock copolymers. Thus, these molecules can be regarded as low molecular weight block compounds consisting of three different and incompatible molecular parts.

  报道了带有侧向亲水基团（如1,2-二醇基、初级和次级酰胺、聚醚链、冠醚单元、糖单位、肼、季铵盐、羧酸和钠盐）的柱状液晶 (p-三苯基衍生物、联苯和p-五苯基衍生物) 的合成及其热驱动液晶特性。通过偏振光显微镜和热量计对这些化合物进行了研究。探讨了极性基团的类型、刚性核心的长度以及亲水基团与杆状刚性核心连接位置的影响。这些两性分子中的许多可以形成单层 S_A 相。如果有足够的氢键相互作用，它们的介相稳定性可能高于其他侧向取代基的相关化合物。对于那些带有较大且灵活的极性侧向取代基（聚醚链）并固定在刚性三苯基单元中心的化合物，可以观察到矩形柱状介相。这些柱状相应代表了由层状相 collapse 所形成的带状相（调制层状相）。所提出的模型也与对三嵌段共聚物超分子结构的建议相关。因此，这些分子可以被视为由三部分不同且不相容的低分子量嵌段化合物。
• Joachimi, Detlev; Tschierske, Carsten; Mueller, Henning, Angewandte Chemie, 1993, vol. 105, # 8, p. 1205 - 1207
  作者：Joachimi, Detlev、Tschierske, Carsten、Mueller, Henning、Wendorff, Joachim Heinz、Schneider, Ludolf、Kleppinger, Ralf

  DOI：——

  日期：——
• Methylene Acetal Formation from 1,2- and 1,3-Diols Using an <i>O</i>,<i>S</i>-Acetal, 1,3-Dibromo-5,5-dimethylhydantoin, and BHT
  作者：Tomohiro Maegawa、Yasuyuki Koutani、Kazuki Otake、Hiromichi Fujioka

  DOI：10.1021/jo4000256

  日期：2013.4.5

  A mild and efficient method for formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT) is described. The use of BHT in this process suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.

  描述了使用甲氧基甲基苯硫醚，1,3-二溴-5,5-二甲基乙内酰脲（DBDMH）和二丁基羟基甲苯（BHT）由1,2-和1,3-二醇形成亚甲基缩醛的温和有效方法。在该方法中使用BHT可抑制副反应，并能高产形成各种二醇（包括碳水化合物型底物）的亚甲基缩醛。
• Selective Deprotection of Methylene Acetal and MOM Ether in the Presence of Ketal-Type Protective Groups: Remarkable Effect of TBSOTf
  作者：Hiromichi Fujioka、Tomohiro Maegawa、Yasuyuki Koutani、Kento Senami、Kenzo Yahata

  DOI：10.3987/com-12-s(n)43

  日期：——

  A novel procedure for highly selective deprotection of methylene acetals and MOM (methoxymethyl) groups in the presence of ketal-type protective groups has been developed. The method, which utilizes a combination of TBSOTf and 2,2'-bipyridyl, displays a completely opposite selectivity compared with those of acid-mediated deprotection protocols.