3-Brompropylphosphorsaeuredichlorid | 56824-07-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 3-Brompropylphosphorsaeuredichlorid
• 英文别名: phosphorodichloridic acid 3-bromo-propyl ester；3-bromopropylphosphoric acid dichloride；γ-Brompropylphosphorsaeuredichlorid；Phosphorsaeure-3-brompropylester-dichlorid；3-Bromopropyl phosphorodichloridate；1-bromo-3-dichlorophosphoryloxypropane
• CAS: 56824-07-8
• 化学式: C₃H₆BrCl₂O₂P
• 分子量: 255.863
• InChiKey: IJYVSIRZSSMJJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  287.7±23.0 °C(Predicted)
• 密度：
  1.770±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Brompropylphosphorsaeuredichlorid 、 二(2-氯乙基)胺盐酸盐 生成 3-bromopropyl bis(2-chloroethyl)phosphoramidochloridate
  参考文献：
  名称：

  N-芳基取代环磷酰胺衍生物的合成尝试

  摘要：

  磷酸-[二-(2-氯乙基)]-酰胺-二氯化物(3)在环磷酰胺合成条件下与氧代-(4-甲氧基苯基)-[4-(3-羟丙基)-氨基苯基]-甲烷反应( 10 ) 不是环磷酰胺衍生物 11 的形成，而是氧代-(4-甲氧基-苯基)-[4-(3-氯丙基)-氨基苯基]-甲烷(12)。在无水溶液和三乙胺存在下，磷酸 3-溴丙酯 [二-(2-氯乙基)] 酰胺氯化物 (14) 与苯胺和磷酸苯胺 [二-(2-氯乙基)] 酰胺氯化物 (15)用 3-溴-1-丙醇环化得到 N-苯基-环磷酰胺 (17)。相反，只有开环磷酸3-溴丙基酯苯胺[二-(2-氯乙基)]酰胺(16)可以从两种反应混合物中分离。描述了从氧代-（4-羟基苯基）-（4-硝基苯基）-甲烷（4）通过 5-9 合成 10；(14)由3-溴-1-丙醇通过13和15由3和苯胺制备。

  DOI：

  10.1002/ardp.19753080408
• 作为产物：
  描述：

  3-溴-1-丙醇 在 三氯氧磷 作用下， 以 四氯化碳 为溶剂， 生成 3-Brompropylphosphorsaeuredichlorid
  参考文献：
  名称：

  N-芳基取代环磷酰胺衍生物的合成尝试

  摘要：

  磷酸-[二-(2-氯乙基)]-酰胺-二氯化物(3)在环磷酰胺合成条件下与氧代-(4-甲氧基苯基)-[4-(3-羟丙基)-氨基苯基]-甲烷反应( 10 ) 不是环磷酰胺衍生物 11 的形成，而是氧代-(4-甲氧基-苯基)-[4-(3-氯丙基)-氨基苯基]-甲烷(12)。在无水溶液和三乙胺存在下，磷酸 3-溴丙酯 [二-(2-氯乙基)] 酰胺氯化物 (14) 与苯胺和磷酸苯胺 [二-(2-氯乙基)] 酰胺氯化物 (15)用 3-溴-1-丙醇环化得到 N-苯基-环磷酰胺 (17)。相反，只有开环磷酸3-溴丙基酯苯胺[二-(2-氯乙基)]酰胺(16)可以从两种反应混合物中分离。描述了从氧代-（4-羟基苯基）-（4-硝基苯基）-甲烷（4）通过 5-9 合成 10；(14)由3-溴-1-丙醇通过13和15由3和苯胺制备。

  DOI：

  10.1002/ardp.19753080408

文献信息

• Steroids for the treatment of hypercholesterolemia
  申请人：Hoffmann-La Roche Inc.

  公开号：US04680290A1

  公开（公告）日：1987-07-14

  Steroids of the formula ##STR1## wherein n represents the number 2, 3 or 4; R.sup.1 represents hydrogen, lower-alkyl or lower-alkylidene; R.sup.2, R.sup.3 and R.sup.4 represent hydrogen or lower-alkyl and the dotted C--C bonds in the 5(6)-, 7(8)-, 22(23)-, 24(28)- and 25(26)-position are optional, whereby the B-ring can contain only one double bond and the side-chain is either saturated or is mono-unsaturated or is di-unsaturated in the 22(23), 25(26)-position; and whereby R.sup.1 is lower-alkyl or lower-alkylidene when a 5(6)-double bond is present, n is 2 and R.sup.2, R.sup.3 and R.sup.4 are methyl, and pharmaceutically acceptable salts of these steroids have activity inhibiting the intestinal resorption of cholesterol. They can be manufactured from steroids which are otherwise substituted in the 3.beta.-position.

  公式为##STR1##的类固醇，其中n代表数字2、3或4；R1代表氢、低碳基或低碳基亚甲基；R2、R3和R4代表氢或低碳基，5（6）位、7（8）位、22（23）位、24（28）位和25（26）位的点状C-C键是可选的，其中B环只能含有一个双键，侧链可以是饱和的，也可以是单不饱和的或双不饱和的，在22（23）位和25（26）位；当5（6）位存在双键时，R1为低碳基或低碳基亚甲基，n为2，R2、R3和R4为甲基，这些类固醇的药物可接受的盐具有抑制胆固醇肠道吸收的活性。它们可以从在3β位上被其他取代的类固醇中制造出来。
• Kertscher, P.; Rueger, H.-J.; Gawrisch, K., Pharmazie, 1980, vol. 35, # 1, p. 10 - 14
  作者：Kertscher, P.、Rueger, H.-J.、Gawrisch, K.、Nuhn, P.、Weissflog, R.

  DOI：——

  日期：——
• Structure—activity relationships for enhancement of paracellular permeability by 2-alkoxy-3-alkylamidopropylphosphocholines across Caco-2 cell monolayers
  作者：Dong-Zhou Liu、Susan L. Morris-Natschke、Louis S. Kucera、Khalid S. Ishaq、Dhiren R. Thakker

  DOI：10.1021/js9900957

  日期：1999.11

  The oral route is the preferred route of delivery for a large number of drug molecules. However, the intestinal epithelium presents a formidable barrier for delivery of drugs into systemic circulation. Phospholipids are among compounds that enhance the absorption of drugs across the intestinal epithelium. In this paper, we describe structure-activity relationships for phospholipid derivatives as enhancers of paracellular permeability across Caco-2 cell monolayers. in a series of 2-alkoxy-3-alkylamidopropylphosphocholine derivatives, compounds with a long chain at C-3 (R-3) and short chain at C-2 (R-2) were potent in causing a decrease in transepithelial electrical resistance (TEER) and an increase in mannitol transport, but also showed significant cytotoxicity. Compounds with 9-11 carbons at C-3 and 6-10 carbons at C-2 provided good separation (up to 2.7-fold) between activity and cytotoxicity. Notably, a good correlation (r(2) = 0.93) was observed between EC50 (TEER) [concentration that caused a drop in TEER to 50% of its control (untreated) value] and EC10X (mannitol) [concentration that caused 10-fold increase in mannitol transport over the control (untreated) value], confirming that a decrease in TEER is associated with enhanced permeability of the hydrophilic compounds across Caco-2 cell monolayers. Compounds with medium to long carbon chains at C-2 and C-3, and the total carbons in the alkyl chains > 20, showed poor activity and no cytotoxicity.
• Analogs of platelet activating factor. 4. Some modifications of the phosphocholine moiety
  作者：A. Wissner、R. E. Schaub、P. E. Sum、C. A. Kohler、B. M. Goldstein

  DOI：10.1021/jm00153a005

  日期：1986.3

  Racemic analogues of platelet activating factor (PAF) in which the methylene bridge separating the phosphate and trimethylammonium moieties is altered in length (7a-f) have been prepared. Increasing the length of this bridge results in a progressive decrease in the hypotensive and platelet aggregation responses. Analogues in which the phosphocholine group is substituted with a methyl group (7h and 7i) or a phenyl group (5j) or in which the methylene bridge is replaced with a meta-substituted benzyl group (5k) have been prepared. With respect to both the blood pressure and platelet aggregation responses, 7i and 5k showed little if any changes in potency compared to racemic C16-PAF (1a). While 7h is more potent than 1a with respect to both the hypotensive and platelet aggregation properties, 5j is less potent. Replacement of the phosphate moiety of C18-PAF (1b) with a phosphonate group (7g) leads to decreased activity in both assays. Analogue 11, in which the phosphocholine group has been replaced with a 4-(trimethylammonio)butoxy group, exhibited no detectable hypotensive or platelet aggregating activity. None of the analogues exhibited a separation of the blood pressure and platelet aggregation activities.
• Kertscher; Ostermann, Pharmazie, 1991, vol. 46, # 10, p. 708 - 711
  作者：Kertscher、Ostermann

  DOI：——

  日期：——