1-(5,27,30,35-Tetramethoxy-16-prop-2-enylspiro[7,11,21,25-tetraoxapentacyclo[24.2.2.23,6.212,15.217,20]hexatriaconta-1(29),3,5,12(34),13,15(33),17,19,26(30),27,31,35-dodecaene-2,4'-piperidine]-1'-yl)ethanone | 577994-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(5,27,30,35-Tetramethoxy-16-prop-2-enylspiro[7,11,21,25-tetraoxapentacyclo[24.2.2.23,6.212,15.217,20]hexatriaconta-1(29),3,5,12(34),13,15(33),17,19,26(30),27,31,35-dodecaene-2,4'-piperidine]-1'-yl)ethanone
• 英文别名: 1-(5,27,30,35-tetramethoxy-16-prop-2-enylspiro[7,11,21,25-tetraoxapentacyclo[24.2.2.23,6.212,15.217,20]hexatriaconta-1(29),3,5,12(34),13,15(33),17,19,26(30),27,31,35-dodecaene-2,4'-piperidine]-1'-yl)ethanone
• CAS: 577994-63-9
• 化学式: C₄₅H₅₃NO₉
• 分子量: 751.917
• InChiKey: UPXPFGPJDVQETC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  55
• 可旋转键数：
  6
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(5,27,30,35-Tetramethoxy-16-prop-2-enylspiro[7,11,21,25-tetraoxapentacyclo[24.2.2.23,6.212,15.217,20]hexatriaconta-1(29),3,5,12(34),13,15(33),17,19,26(30),27,31,35-dodecaene-2,4'-piperidine]-1'-yl)ethanone 在 dimethyl sulfide borane 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到1-(10'-(3-hydroxypropyl)-3',3',5',5'-tetramethoxyspiro[piperidine-4,2'-4,8,12,16-tetraoxa-1,3,9,11(1,4)-tetrabenzenacyclohexadecaphan]-1-yl)ethan-1-one
  参考文献：
  名称：

  Host−[2]Rotaxanes as Cellular Transport Agents

  摘要：

  Host-[2)rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K-A's) in the range of 1 x 10(4) to 5 x 104 M-1, whereas the K-A range for the fluorophores is 1 x 10(4) to 9 x 10(5) m(-1). Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 x 10(3) to 5 x 10(3) m(-1) range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane-[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft-[2)rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.

  DOI：

  10.1021/ja034918c
• 作为产物：
  描述：

  4,4'-二羟基二苯甲酮 在 sodium tetrahydroborate 、 lithium di-tert-butylbiphenylide 、 potassium carbonate 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 1-(5,27,30,35-Tetramethoxy-16-prop-2-enylspiro[7,11,21,25-tetraoxapentacyclo[24.2.2.23,6.212,15.217,20]hexatriaconta-1(29),3,5,12(34),13,15(33),17,19,26(30),27,31,35-dodecaene-2,4'-piperidine]-1'-yl)ethanone
  参考文献：
  名称：

  Host−[2]Rotaxanes as Cellular Transport Agents

  摘要：

  Host-[2)rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K-A's) in the range of 1 x 10(4) to 5 x 104 M-1, whereas the K-A range for the fluorophores is 1 x 10(4) to 9 x 10(5) m(-1). Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 x 10(3) to 5 x 10(3) m(-1) range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane-[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft-[2)rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.

  DOI：

  10.1021/ja034918c

文献信息

• Host−[2]Rotaxanes as Cellular Transport Agents
  作者：Vadims Dvornikovs、Brian E. House、Marcia Kaetzel、John R. Dedman、David B. Smithrud

  DOI：10.1021/ja034918c

  日期：2003.7.1

  Host-[2)rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K-A's) in the range of 1 x 10(4) to 5 x 104 M-1, whereas the K-A range for the fluorophores is 1 x 10(4) to 9 x 10(5) m(-1). Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 x 10(3) to 5 x 10(3) m(-1) range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane-[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft-[2)rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.