(E)-4-acetoxy-3-methyl-2-phytyl-1-naphthaleneol

• 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: (E)-4-acetoxy-3-methyl-2-phytyl-1-naphthaleneol
• 英文别名: (E)-4-acetoxy-3-methyl-2-phytyl-1-naphthalenol；[4-hydroxy-2-methyl-3-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalen-1-yl] acetate
• 化学式: C₃₃H₅₀O₃
• 分子量: 494.758
• InChiKey: SHKSHVHAEZZSCS-YYADALCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-acetoxy-3-methyl-2-phytyl-1-naphthaleneol 生成 [4-[4-acetyloxy-3-methyl-2-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalen-1-yl]oxy-2-methyl-3-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalen-1-yl] acetate
  参考文献：
  名称：

  SOKOLOVA, N. A.;BYZOVA, V. N.;SARYCHEVA, I. K.;EVSTIGNEEVA, R. P., XIM.-FARMATS. ZH., 1985, 19, N 8, 995-998

  摘要：

  DOI：
• 作为产物：
  描述：

  维生素 K4 在 ammonium hydroxide 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 生成 (E)-4-acetoxy-3-methyl-2-phytyl-1-naphthaleneol
  参考文献：
  名称：

  维生素K氧化的热化学研究

  摘要：

  萘氢醌阴离子的新氧化反应的发现使得测定氧与钾盐的反应热 (ΔH ox ) 成为可能，该钾盐源自维生素 K 的氢醌形式的去质子化。从该值 (-33.52±0.60 kcal/mol )、维生素 KH 2 的去质子化热 (-30.03±1.20 kcal/mol) 和水的去质子化热 (-6.05±0.3 kcal/mol)，维生素 KH 2 转化为维生素 K 氧化物的焓变为确定为 -57.5 kcal/mol，与我们之前估计的母体萘氢醌氧化的 -62.4 kcal/mol 合理一致

  DOI：

  10.1021/ja00074a006

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.
• AREFEVA, I. V.;ZHUKOVA, E. EH.;BYZOVA, V. N.;EVSTIGNEEVA, R. P., BCEC. KONF. PO XIMII XINONOV I XINOID. SOED., KRASNOYARSK, 3-5 IYULYA, 19+
  作者：AREFEVA, I. V.、ZHUKOVA, E. EH.、BYZOVA, V. N.、EVSTIGNEEVA, R. P.

  DOI：——

  日期：——
• Thermochemical investigation of the oxygenation of vitamin K
  作者：Robert A. Flowers、Sriram Naganathan、Paul Dowd、Edward M. Arnett、Seung Wook Ham

  DOI：10.1021/ja00074a006

  日期：1993.10

  oxygen with the potassium salt derived from deprotonation of the hydroquinone form of vitamin K. From that value (-33.52±0.60 kcal/mol), the heat of deprotonation of vitamin KH 2 (-30.03±1.20 kcal/mol), and the heat of deprotonation of water (-6.05±0.3 kcal/mol), the enthalpy change for converting vitamin KH 2 to vitamin K oxide is established to be -57.5 kcal/mol, in reasonable agreement with our previous

  萘氢醌阴离子的新氧化反应的发现使得测定氧与钾盐的反应热 (ΔH ox ) 成为可能，该钾盐源自维生素 K 的氢醌形式的去质子化。从该值 (-33.52±0.60 kcal/mol )、维生素 KH 2 的去质子化热 (-30.03±1.20 kcal/mol) 和水的去质子化热 (-6.05±0.3 kcal/mol)，维生素 KH 2 转化为维生素 K 氧化物的焓变为确定为 -57.5 kcal/mol，与我们之前估计的母体萘氢醌氧化的 -62.4 kcal/mol 合理一致
• SOKOLOVA, N. A.;BYZOVA, V. N.;SARYCHEVA, I. K.;EVSTIGNEEVA, R. P., XIM.-FARMATS. ZH., 1985, 19, N 8, 995-998
  作者：SOKOLOVA, N. A.、BYZOVA, V. N.、SARYCHEVA, I. K.、EVSTIGNEEVA, R. P.

  DOI：——

  日期：——