12-[4-(12-hydroxydodecyloxy)phenoxy]dodecan-1-ol | 209588-75-0

• 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-[4-(12-hydroxydodecyloxy)phenoxy]dodecan-1-ol
• 英文别名: 12-[4-(12-Hydroxydodecoxy)phenoxy]dodecan-1-ol；12-[4-(12-hydroxydodecoxy)phenoxy]dodecan-1-ol
• CAS: 209588-75-0
• 化学式: C₃₀H₅₄O₄
• 分子量: 478.756
• InChiKey: CAZSKRHIOFRIIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  598.155±20.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.966±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  34
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-[4-(12-hydroxydodecyloxy)phenoxy]dodecan-1-ol 在 2-碘酰苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 12.0h， 以70%的产率得到12-[4-(11-formylundecyloxy)phenoxy]dodecanal
  参考文献：
  名称：

  Chiral recognition in aggregates formed by chiral bola-amphiphiles

  摘要：

  The aggregates of three new isomeric chiral bola-amphiphiles have been taken into consideration as models for investigating chiral recognition in biological membranes. The recognition capabilities of the aggregates were explored following (by CD and HPLC experiments) the shift in the equilibrium between the inter-converting enantiomers of a biphenylic derivative and bilirubin, used as markers of chirality. The chiral recognition experiments were performed under different pH and concentration conditions. The results were compared with those relative to the aggregates formed by an equimolar mixture of single head/single chain amphiphiles that mimic the structure of the bola surfactant devoid of a covalent link. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2010.07.002
• 作为产物：
  描述：

  1,4-Bis-[12-(tert-butyl-dimethyl-silanyloxy)-dodecyloxy]-benzene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以91%的产率得到12-[4-(12-hydroxydodecyloxy)phenoxy]dodecan-1-ol
  参考文献：
  名称：

  Preparation ofα,ω-Diols of Long Carbon Chains and Their Use in Polyurethane Synthesis

  摘要：

  NaH 促进 HO(CH2)12O–TBDMS (1, TBDMS=SiMe2(t-Bu)) 和 Br(CH2)12O–TBDMS (2) 的偶联反应，然后有机甲硅烷基脱保护，得到 HO(CH2)12O(CH2) )12OH (5)。 1,12-十二烷二醇在 NaH 存在下与过量的 2 反应，生成 TBDMS–O(CH2)12O(CH2)12O(CH2)12O–TBDMS (6)，然后转化为 HO(CH2)12O(CH2) )12O(CH2)12OH (7) 通过除去保护基团。对苯二酚与 2 和 Br(CH2)6O–TBDMS (3) 进行类似的 1:2 缩合，会形成相应的 α,ω-二醇、HO(CH2)12OC6H4O(CH2)12OH (9) 和 HO(CH2)分别为 6OC6H4O(CH2)6OH (11)。通过红外光谱、核磁共振光谱以及元素分析，分离并表征了四种新的长 α,ω-二醇。 5、7、9 和 11 与 1,3-双(异氰酸甲酯基)苯和 1,1'-亚甲基双[4-异氰酸甲酯基苯]的加聚反应可以高产率得到相应的聚(聚氨酯)。所获得的聚合物通过IR和NMR光谱进行表征，根据使用聚苯乙烯标准的凝胶渗透色谱测定其分子量超过20000。

  DOI：

  10.1246/bcsj.71.1477

文献信息

• Preparation of<i>α,ω</i>-Diols of Long Carbon Chains and Their Use in Polyurethane Synthesis
  作者：Kohtaro Osakada、Yasumasa Takenaka、Isao Yamaguchi、Takakazu Yamamoto

  DOI：10.1246/bcsj.71.1477

  日期：1998.6

  NaH promoted coupling reaction of HO(CH2)12O–TBDMS (1, TBDMS=SiMe2(t-Bu)) and Br(CH2)12O–TBDMS (2) followed by deprotection of the organosilyl groups affords HO(CH2)12O(CH2)12OH (5). 1,12-Dodecanediol reacts with an excess amount of 2 in the presence of NaH to give TBDMS–O(CH2)12O(CH2)12O(CH2)12O–TBDMS (6) which is turned into HO(CH2)12O(CH2)12O(CH2)12OH (7) by removal of the protecting groups. Similar 1 : 2 condensation of hydroquinone with 2 and with Br(CH2)6O–TBDMS (3) leads to formation of the corresponding α,ω-diols, HO(CH2)12OC6H4O(CH2)12OH (9) and HO(CH2)6OC6H4O(CH2)6OH (11), respectively. The four new long α,ω-diols are isolated and characterized by means of IR and NMR spectroscopy as well as elemental analyses. Polyaddition reactions of 5, 7, 9, and 11 to 1,3-bis(isocyanatomethyl)benzene and 1,1′-methylenebis[4-isocyanatobenzene] give the corresponding poly(urethane)s in high yields. The obtained polymers, which were characterized by IR and NMR spectroscopy, have molecular weights over 20000 as determined from gel permeation chromatography using polystyrene standards.

  NaH 促进 HO(CH2)12O–TBDMS (1, TBDMS=SiMe2(t-Bu)) 和 Br(CH2)12O–TBDMS (2) 的偶联反应，然后有机甲硅烷基脱保护，得到 HO(CH2)12O(CH2) )12OH (5)。 1,12-十二烷二醇在 NaH 存在下与过量的 2 反应，生成 TBDMS–O(CH2)12O(CH2)12O(CH2)12O–TBDMS (6)，然后转化为 HO(CH2)12O(CH2) )12O(CH2)12OH (7) 通过除去保护基团。对苯二酚与 2 和 Br(CH2)6O–TBDMS (3) 进行类似的 1:2 缩合，会形成相应的 α,ω-二醇、HO(CH2)12OC6H4O(CH2)12OH (9) 和 HO(CH2)分别为 6OC6H4O(CH2)6OH (11)。通过红外光谱、核磁共振光谱以及元素分析，分离并表征了四种新的长 α,ω-二醇。 5、7、9 和 11 与 1,3-双(异氰酸甲酯基)苯和 1,1'-亚甲基双[4-异氰酸甲酯基苯]的加聚反应可以高产率得到相应的聚(聚氨酯)。所获得的聚合物通过IR和NMR光谱进行表征，根据使用聚苯乙烯标准的凝胶渗透色谱测定其分子量超过20000。
• Chiral recognition in aggregates formed by chiral bola-amphiphiles
  作者：Francesca Ceccacci、Pietro di Profio、Luisa Giansanti、Stefano Levi Mortera、Giovanna Mancini、Alessandro Sorrenti、Claudio Villani

  DOI：10.1016/j.tetasy.2010.07.002

  日期：2010.9

  The aggregates of three new isomeric chiral bola-amphiphiles have been taken into consideration as models for investigating chiral recognition in biological membranes. The recognition capabilities of the aggregates were explored following (by CD and HPLC experiments) the shift in the equilibrium between the inter-converting enantiomers of a biphenylic derivative and bilirubin, used as markers of chirality. The chiral recognition experiments were performed under different pH and concentration conditions. The results were compared with those relative to the aggregates formed by an equimolar mixture of single head/single chain amphiphiles that mimic the structure of the bola surfactant devoid of a covalent link. (C) 2010 Published by Elsevier Ltd.