Dihydro-Vitamin-K1-diacetat | 604-87-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Dihydro-Vitamin-K1-diacetat
• 英文别名: [4-acetyloxy-2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)naphthalen-1-yl] acetate
• CAS: 604-87-5；5016-88-6；52610-74-9
• 化学式: C₃₅H₅₂O₄
• 分子量: 536.795
• InChiKey: OMMWEESMXJLLLQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  9.93
• 重原子数：
  39.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Dihydro-Vitamin-K1-diacetat 在 sodium hydroxide 、 potassium hydride 作用下， 以 乙醇 为溶剂， 反应 2.08h， 生成 4-methoxy-3-methyl-2-phytyl-1-naphthalenol
  参考文献：
  名称：

  The Active Site of Vitamin K and the Role of the Vitamin K-Dependent Carboxylase

  摘要：

  Vitamin K is the blood-clotting vitamin. It participates in the blood coagulation cascade as a carboxylase cofactor. Enzymic oxygenation of vitamin K hydroquinone provides the driving force for the carboxylation of selected glutamates in the proteins of the blood-clotting cascade. The active site of vitamin K has now been defined by O-18-labeling experiments. The oxygenation is completely specific for the carbonyl group adjacent to the quinone methyl group of vitamin K. The experiment makes use of the O-18-labeled vitamin K isotopomers 9 and 10. Thus, oxygenation of 9 with O-16(2) occurs at the carbonyl group next to methyl, as shown by exchange of the O-18 label at that position. Synthesis of the two O-18-labeled vitamin K isotopomers 9 and 10 was accomplished by cerium(IV)-mediated oxidation in the presence of (H2O)-O-18 of the corresponding methyl half-ethers 4 and 8. The position of the label was ascertained by C-13 and heteronuclear NOE NMR spectroscopies. A role for the active site thiols on the vitamin K-dependent carboxylase is also suggested. The thiolate anion is an excellent candidate for the weak base that initiates the base strength amplification sequence leading to carboxylation and vitamin K oxide formation.

  DOI：

  10.1021/ja00101a003
• 作为产物：
  描述：

  1,4-二乙酰氧基-2-溴-3-甲基萘 、 phytyl bromide 生成 Dihydro-Vitamin-K1-diacetat
  参考文献：
  名称：

  维生素K的新合成

  摘要：

  描述了一种新的有效合成维生素K 1（1）和K 2（5）（2 ; n = 1）的方法，该方法使用π-烯丙基镍（I）配合物。已经研究了溶剂效应和反式-立体选择性。

  DOI：

  10.1039/c3972000953a

文献信息

• The Active Site of Vitamin K and the Role of the Vitamin K-Dependent Carboxylase
  作者：Sriram Naganathan、Roger Hershline、Seung Wook Ham、Paul Dowd

  DOI：10.1021/ja00101a003

  日期：1994.11

  Vitamin K is the blood-clotting vitamin. It participates in the blood coagulation cascade as a carboxylase cofactor. Enzymic oxygenation of vitamin K hydroquinone provides the driving force for the carboxylation of selected glutamates in the proteins of the blood-clotting cascade. The active site of vitamin K has now been defined by O-18-labeling experiments. The oxygenation is completely specific for the carbonyl group adjacent to the quinone methyl group of vitamin K. The experiment makes use of the O-18-labeled vitamin K isotopomers 9 and 10. Thus, oxygenation of 9 with O-16(2) occurs at the carbonyl group next to methyl, as shown by exchange of the O-18 label at that position. Synthesis of the two O-18-labeled vitamin K isotopomers 9 and 10 was accomplished by cerium(IV)-mediated oxidation in the presence of (H2O)-O-18 of the corresponding methyl half-ethers 4 and 8. The position of the label was ascertained by C-13 and heteronuclear NOE NMR spectroscopies. A role for the active site thiols on the vitamin K-dependent carboxylase is also suggested. The thiolate anion is an excellent candidate for the weak base that initiates the base strength amplification sequence leading to carboxylation and vitamin K oxide formation.
• New synthesis of vitamin K
  作者：Kikumasa Sato、Seiichi Inoue、Kenji Saito

  DOI：10.1039/c3972000953a

  日期：——

  A new and effective synthesis of vitamin K1(1) and K2(5), (2; n= 1), is described, using a π-allylic nickel(I) complex; solvent effects and the trans-stereoselectivity have been investigated.

  描述了一种新的有效合成维生素K 1（1）和K 2（5）（2 ; n = 1）的方法，该方法使用π-烯丙基镍（I）配合物。已经研究了溶剂效应和反式-立体选择性。