2,2-dimethyl-1,3-propanediol 4-octylphenylboronate | 876292-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dimethyl-1,3-propanediol 4-octylphenylboronate
• 英文别名: 2,2-dimethyl-1,3-propanediyl 4-octylphenylboronate；5,5-dimethyl-2-(4-octylphenyl)-1,3,2-dioxaborinane
• CAS: 876292-95-4
• 化学式: C₁₉H₃₁BO₂
• 分子量: 302.265
• InChiKey: ILPABLSJJBKESF-UHFFFAOYSA-N

物化性质

• 熔点：
  44-46 °C
• 沸点：
  407.0±24.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1,3-propanediol 4-octylphenylboronate 在 chloroamine-T 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.58h， 以98%的产率得到4-n-octyliodobenzene
  参考文献：
  名称：

  Flexible and enantioselective access to jaspine B and biologically active chain-modified analogues thereof

  摘要：

  尽管细胞毒性物质anhydrophytosphingosine jaspine B的全顺式四氢呋喃骨架被认为是相关药效基团，但对于这种两亲性分子中的脂肪链对其活性的影响却知之甚少。我们开发了一种合成策略，允许在jaspine的骨架中灵活引入各种亲脂性片段。这条路线通过两种不同的方法验证了jaspine B的合成。我们还制备了五个经过链修饰的类似物。这些衍生物的生物学评价显示，它们的细胞毒性与抑制黑色素瘤细胞中神经酰胺转化为鞘磷脂的能力之间存在良好的相关性。因此，我们鉴定出一组强效且选择性的鞘磷脂生产抑制剂。此外，一个ω-氨基化类似物表现出的良好整体效能，使我们能够将jaspine B的药理作用与其两亲性本质分离。

  DOI：

  10.1039/c004218h
• 作为产物：
  描述：

  1-(4-溴苯基)辛烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,2-dimethyl-1,3-propanediol 4-octylphenylboronate
  参考文献：
  名称：

  Self-Assembled Fluorescent Hexaazatriphenylenes That Act as a Light-Harvesting Antenna

  摘要：

  In this paper we report the self-assembling nature of fluorescent hexaazatriphenylenes (HATs) 6a-d with six alkyl/alkoxy-chain-containing biphenyl groups and their application to light-harvesting antennae. In a nonpolar solvent and the film state, the HAT derivatives form one-dimensional aggregates with an H-type parallel stacking mode, which were analyzed by H-1 NMR, UV-vis, and steady-state and time-resolved fluorescence spectroscopy. When HAT derivative 7 with six perylenediimide moieties is incorporated into the one-dimensional aggregates, an efficient energy transfer takes place from the self-assembled HAT moiety as a light-harvesting antenna to the perylenediimide moiety as an energy acceptor. Further, when HAT derivative 8 with six triphenylamino moieties is newly added to the light-harvesting system, an intermolecular electron transfer occurs subsequently between the electron-accepting perylenediimide molecule and the electron-donating triphenylamino molecule.

  DOI：

  10.1021/jo060768n

文献信息

• Expanded π-Electron Systems, Tri(phenanthro)hexaazatriphenylenes and Tri(phenanthrolino)hexaazatriphenylenes, That Are Self-Assembled To Form One-Dimensional Aggregates
  作者：Tsutomu Ishi-i、Ryoichi Hirashima、Naotaka Tsutsumi、Shogo Amemori、Shigeki Matsuki、Yuuki Teshima、Rempei Kuwahara、Shuntaro Mataka

  DOI：10.1021/jo101212d

  日期：2010.10.15

  This paper reports the self-assembling and electrochemical nature of hexaazatriphenylene-based electron-deficient heteroaromatics with an expanded pi-electron system The tri(phenanthro)hexaazatriphenylenes (TPHAT-Cs) and tri(phenanthrolino)hexaazatriphenylenes (TPHAT-Ns) were prepared by condensation reactions or the corresponding phenanthrenequinonones and phenanthrolinediones respectively. with hexaaminobenzene Their election affinity was indicated from cyclic voltammetry measurements. In which the first reduction potentials were evaluated at mound -1 7 V (vs Fc/Fe+) in dichloromethane In nonpolar and polar solvents and in the film state. the TPHAT-Cs and TPHAT-Ns formed one-dimensional aggregates with an H-type stacking mode. In the MALDI-TOF mass spectra significant peaks were seen at several multiples of the parent ion up to tell;liner aggregates The NMR spectra indicated a line-broadening effect due to the aggregation The UV-vis and fluorescence spectra showed a concentration dependence which is. attributed to a dynamic exchange between the monomer and aggregate species The older of the aggregative nature was estimated from the concentration dependence and the fluorescence quantum yield By replacement of the peripheral aromatic moieties instead of the phenanthiene (TPHAT-Cs) with the phenanthroline (TPHAT-Ns). the aggregative nature was enhanced
• Self-Assembling of n-Type Semiconductor Tri(phenanthrolino)hexaazatriphenylenes with a Large Aromatic Core
  作者：Tsutomu Ishi-i、Kentaro Yaguma、Rempei Kuwahara、Yoshiki Taguri、Shuntaro Mataka

  DOI：10.1021/ol052779t

  日期：2006.2.1

  Large disk-shaped aromatic tri(phenanthrolino)hexaazatriphenylenes 5a, 5b, and 5c with six butyl, dodecyl, and 4-octylphenyl groups, respectively, were self-assembled both in solution and film state to form one-dimensional aggregates. Their n-type semiconducting nature was indicated from CV measurement, in which the first reduction potentials were evaluated at around -1.7 V (vs Fc/Fc(+)) in dichloromethane.
• Flexible and enantioselective access to jaspine B and biologically active chain-modified analogues thereof
  作者：Yahya Salma、Stéphanie Ballereau、Carine Maaliki、Sonia Ladeira、Nathalie Andrieu-Abadie、Yves Génisson

  DOI：10.1039/c004218h

  日期：——

  Whereas the all-cis tetrahydrofuran framework of the cytotoxic anhydrophytosphingosine jaspine B is considered as a relevant pharmacophore, little is known about the influence of the aliphatic chain of this amphiphilic molecule on its activity. We developed a synthetic strategy allowing flexible introduction of various lipophilic fragments in the jaspine's skeleton. The route was validated with two distinct approaches to jaspine B. Five chain-modified analogues were also prepared. Biological evaluation of these derivatives demonstrated a good correlation between their cytotoxicity and their capacity to inhibit conversion of ceramide into sphingomyelin in melanoma cells. A series of potent and selective inhibitors of sphingomyelin production was thus identified. Furthermore, the good overall potency of an ω-aminated analogue allowed us to dissociate of the pharmacological action of jaspine B from its amphiphilic nature.

  尽管细胞毒性物质anhydrophytosphingosine jaspine B的全顺式四氢呋喃骨架被认为是相关药效基团，但对于这种两亲性分子中的脂肪链对其活性的影响却知之甚少。我们开发了一种合成策略，允许在jaspine的骨架中灵活引入各种亲脂性片段。这条路线通过两种不同的方法验证了jaspine B的合成。我们还制备了五个经过链修饰的类似物。这些衍生物的生物学评价显示，它们的细胞毒性与抑制黑色素瘤细胞中神经酰胺转化为鞘磷脂的能力之间存在良好的相关性。因此，我们鉴定出一组强效且选择性的鞘磷脂生产抑制剂。此外，一个ω-氨基化类似物表现出的良好整体效能，使我们能够将jaspine B的药理作用与其两亲性本质分离。
• Self-Assembled Fluorescent Hexaazatriphenylenes That Act as a Light-Harvesting Antenna
  作者：Tsutomu Ishi-i、Koh-ichi Murakami、Yusuke Imai、Shuntaro Mataka

  DOI：10.1021/jo060768n

  日期：2006.7.1

  In this paper we report the self-assembling nature of fluorescent hexaazatriphenylenes (HATs) 6a-d with six alkyl/alkoxy-chain-containing biphenyl groups and their application to light-harvesting antennae. In a nonpolar solvent and the film state, the HAT derivatives form one-dimensional aggregates with an H-type parallel stacking mode, which were analyzed by H-1 NMR, UV-vis, and steady-state and time-resolved fluorescence spectroscopy. When HAT derivative 7 with six perylenediimide moieties is incorporated into the one-dimensional aggregates, an efficient energy transfer takes place from the self-assembled HAT moiety as a light-harvesting antenna to the perylenediimide moiety as an energy acceptor. Further, when HAT derivative 8 with six triphenylamino moieties is newly added to the light-harvesting system, an intermolecular electron transfer occurs subsequently between the electron-accepting perylenediimide molecule and the electron-donating triphenylamino molecule.